Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents

ABSTRACT

The present invention relates to novel sulfoperoxycarboxylic acid compounds, and methods for making and using them. The sulfoperoxycarboxylic compounds of the invention are storage stable, water soluble and have low to no odor. Further, the compounds of the present invention can be formed from non-petroleum based renewable materials. The compounds of the present invention can be used as antimicrobials, and bleaching agents. The compounds of the present invention are also suitable for use as coupling agents.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation in part of U.S. patent applicationSer. No. 12/413,189, filed on Mar. 27, 2009. U.S. patent applicationSer. No. 12/413,189 claims priority to U.S. Provisional Application Ser.No. 61/040,444, filed on Mar. 28, 2008 and entitled“SULFOPEROXYCARBOXYLIC ACIDS, THEIR PREPARATION AND METHODS OF USE ASBLEACHING AND ANTIMICROBIAL AGENTS.” The entire contents of this patentapplication is hereby expressly incorporated herein by referenceincluding, without limitation, the specification, claims, and abstract,as well as any figures, tables, or drawings thereof.

FIELD OF THE INVENTION

The present invention relates to novel sulfoperoxycarboxylic acidcompounds, compositions, and methods of making and using thesecompounds.

BACKGROUND

Peroxycarboxylic acids are known for use as antimicrobials and bleachingagents. However, conventional peroxycarboxylic acids have inherentdisadvantages of limited storage stability, and water solubility.Further, most peroxycarboxylic acids have an unpleasant odor. Thus, aneed exists for storage stable, low or no odor, water solubleperoxycarboxylic acid compounds and compositions that also possessantimicrobial and bleaching properties.

SUMMARY

In some aspects, the present invention relates to novelsulfoperoxycarboxylic acids, and methods for making them. The compoundsof the invention are storage stable, have low or no-odor, and are watersoluble. Further, the compounds of the present invention can be derivedfrom non-petroleum based, renewable oils.

In some aspects, the present invention provides methods for using thecompounds of the present invention as bleaching and/or antimicrobialagents. In some aspects, the present invention provides methods forusing the compounds of the invention as coupling agents. In someaspects, the present invention provides methods for using the compoundsof the present invention as low foaming bleach hydrotopes for tunnelwashers, and for side loading washing machines.

In some embodiments, the compounds and compositions of the presentinvention are suitable for use as low temperature bleaches, e.g., atabout 40 degrees Celsius. In some embodiments, the compounds of thepresent invention are suitable for use as pH optimized peroxygenbleaches, in combination with alkaline detergents. In some embodiments,the present invention includes a method for using the compounds andcompositions of the present invention as color safe, textile tolerantbleaches for textiles, e.g., wools and cotton.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a graphical depiction of the stability profile ofperoxyoctanoic acid over time when contacted with different testsolutions.

FIG. 2 is a graphical depiction of the stability of an exemplarycomposition of the present invention over time at an elevatedtemperature.

FIG. 3 is a graphical depiction of the ability of selected compositionsof the present invention to stabilize percarboxylic acids over time.

FIG. 4 is a graphical depiction of the bleaching performance ofcompositions of the present invention compared to commercially availablebleaching agents.

FIG. 5 is a graphical depiction of the stability profile ofperoxyoctanoic acid in combination with exemplary compositions of thepresent invention.

FIG. 6 is a graphical depiction of the coupling capabilities of aselected composition of the present invention.

FIG. 7 is a graphical depiction of the stability of selected sulfonatedperacids in aqueous solutions over time.

FIG. 8 is a graphical depiction of the bleaching abilities of selectedsulfonated peracids compared to peroxyacetic acid.

FIG. 9 graphically depicts the efficacy of selected sulfonated peracidsagainst Staphylococcus aureus at ambient temperature.

FIG. 10 graphically depicts the efficacy of selected sulfonated peracidsagainst Escherichia coli at ambient temperature.

DETAILED DESCRIPTION

The present invention relates to sulfoperoxycarboxylic acids of FormulaI, and methods of making and using them. In some embodiments, thesulfoperoxycarboxylic acids of the invention are not sulfonated at theterminal position of the carboxylic acid chain. Unlike conventionalperoxycarboxylic acids, it has been found that the sulfoperoxycarboxylicacids of the present invention are low-odor, water soluble, and storagestable. The compounds of the present invention can be used as a puresolid powder, or blended with additional functional ingredients, forexample, chelators, buffers, or other cleaning agents. They can also beincorporated into liquid formulas. The compounds and compositions of thepresent invention have many uses including, but not limited to,antimicrobials, bleaches, and coupling agents.

So that the invention maybe more readily understood, certain terms arefirst defined.

As used herein, “weight percent,” “wt-%,” “percent by weight,” “% byweight,” and variations thereof refer to the concentration of asubstance as the weight of that substance divided by the total weight ofthe composition and multiplied by 100. It is understood that, as usedhere, “percent,” “%,” and the like are intended to be synonymous with“weight percent,” “wt-%,” etc.

As used herein, the term “about” refers to variation in the numericalquantity that can occur, for example, through typical measuring andliquid handling procedures used for making concentrates or use solutionsin the real world; through inadvertent error in these procedures;through differences in the manufacture, source, or purity of theingredients used to make the compositions or carry out the methods; andthe like. The term “about” also encompasses amounts that differ due todifferent equilibrium conditions for a composition resulting from aparticular initial mixture. Whether or not modified by the term “about”,the claims include equivalents to the quantities.

It should be noted that, as used in this specification and the appendedclaims, the singular forms “a,” “an,” and “the” include plural referentsunless the content clearly dictates otherwise. Thus, for example,reference to a composition containing “a compound” includes acomposition having two or more compounds. It should also be noted thatthe term “or” is generally employed in its sense including “and/or”unless the content clearly dictates otherwise.

As used herein, the phrases “objectionable odor,” “offensive odor,” or“malodor,” refer to a sharp, pungent, or acrid odor or atmosphericenvironment from which a typical person withdraws if they are able to.Hedonic tone provides a measure of the degree to which an odor ispleasant or unpleasant. An “objectionable odor,” “offensive odor,” or“malodor” has an hedonic tone rating it as unpleasant as or moreunpleasant than a solution of 5 wt-% acetic acid, propionic acid,butyric acid, or mixtures thereof.

As used herein, the term “microorganism” refers to any noncellular orunicellular (including colonial) organism. Microorganisms include allprokaryotes. Microorganisms include bacteria (including cyanobacteria),spores, lichens, fungi, protozoa, virinos, viroids, viruses, phages, andsome algae. As used herein, the term “microbe” is synonymous withmicroorganism.

As used herein, the phrase “food product” includes any food substancethat might require treatment with an antimicrobial agent or compositionand that is edible with or without further preparation. Food productsinclude meat (e.g. red meat and pork), seafood, poultry, produce (e.g.,fruits and vegetables), eggs, living eggs, egg products, ready to eatfood, wheat, seeds, roots, tubers, leafs, stems, corns, flowers,sprouts, seasonings, or a combination thereof. The term “produce” refersto food products such as fruits and vegetables and plants orplant-derived materials that are typically sold uncooked and, often,unpackaged, and that can sometimes be eaten raw.

As used herein, the phrase “plant” or “plant product” includes any plantsubstance or plant-derived substance. Plant products include, but arenot limited to, seeds, nuts, nut meats, cut flowers, plants or cropsgrown or stored in a greenhouse, house plants, and the like. Plantproducts include many animal feeds.

As used herein, the phrase “meat product” refers to all forms of animalflesh, including the carcass, muscle, fat, organs, skin, bones and bodyfluids and like components that form the animal. Animal flesh includes,but is not limited to, the flesh of mammals, birds, fishes, reptiles,amphibians, snails, clams, crustaceans, other edible species such aslobster, crab, etc., or other forms of seafood. The forms of animalflesh include, for example, the whole or part of animal flesh, alone orin combination with other ingredients. Typical forms include, forexample, processed meats such as cured meats, sectioned and formedproducts, minced products, finely chopped products, ground meat andproducts including ground meat, whole products, and the like.

As used herein the term “poultry” refers to all forms of any bird kept,harvested, or domesticated for meat or eggs, and including chicken,turkey, ostrich, game hen, squab, guinea fowl, pheasant, quail, duck,goose, emu, or the like and the eggs of these birds. Poultry includeswhole, sectioned, processed, cooked or raw poultry, and encompasses allforms of poultry flesh, by-products, and side products. The flesh ofpoultry includes muscle, fat, organs, skin, bones and body fluids andlike components that form the animal. Forms of animal flesh include, forexample, the whole or part of animal flesh, alone or in combination withother ingredients. Typical forms include, for example, processed poultrymeat, such as cured poultry meat, sectioned and formed products, mincedproducts, finely chopped products and whole products.

As used herein, the phrase “poultry debris” refers to any debris,residue, material, dirt, offal, poultry part, poultry waste, poultryviscera, poultry organ, fragments or combinations of such materials, andthe like removed from a poultry carcass or portion during processing andthat enters a waste stream.

As used herein, the phrase “food processing surface” refers to a surfaceof a tool, a machine, equipment, a structure, a building, or the likethat is employed as part of a food processing, preparation, or storageactivity. Examples of food processing surfaces include surfaces of foodprocessing or preparation equipment (e.g., slicing, canning, ortransport equipment, including flumes), of food processing wares (e.g.,utensils, dishware, wash ware, and bar glasses), and of floors, walls,or fixtures of structures in which food processing occurs. Foodprocessing surfaces are found and employed in food anti-spoilage aircirculation systems, aseptic packaging sanitizing, food refrigerationand cooler cleaners and sanitizers, ware washing sanitizing, blanchercleaning and sanitizing, food packaging materials, cutting boardadditives, third-sink sanitizing, beverage chillers and warmers, meatchilling or scalding waters, autodish sanitizers, sanitizing gels,cooling towers, food processing antimicrobial garment sprays, andnon-to-low-aqueous food preparation lubricants, oils, and rinseadditives.

As used herein, the term “ware” refers to items such as eating andcooking utensils, dishes, and other hard surfaces such as showers,sinks, toilets, bathtubs, countertops, windows, mirrors, transportationvehicles, and floors. As used herein, the term “warewashing” refers towashing, cleaning, or rinsing ware. Ware also refers to items made ofplastic. Types of plastics that can be cleaned with the compositionsaccording to the invention include but are not limited to, those thatinclude polycarbonate polymers (PC), acrilonitrile-butadiene-styrenepolymers (ABS), and polysulfone polymers (PS). Another exemplary plasticthat can be cleaned using the compounds and compositions of theinvention include polyethylene terephthalate (PET).

As used herein, the phrase “air streams” includes food anti-spoilage aircirculation systems. Air streams also include air streams typicallyencountered in hospital, surgical, infirmity, birthing, mortuary, andclinical diagnosis rooms.

As used herein, the term “waters” includes food process or transportwaters. Food process or transport waters include produce transportwaters (e.g., as found in flumes, pipe transports, cutters, slicers,blanchers, retort systems, washers, and the like), belt sprays for foodtransport lines, boot and hand-wash dip-pans, third-sink rinse waters,and the like. Waters also include domestic and recreational waters suchas pools, spas, recreational flumes and water slides, fountains, and thelike.

As used herein, the phrase “health care surface” refers to a surface ofan instrument, a device, a cart, a cage, furniture, a structure, abuilding, or the like that is employed as part of a health careactivity. Examples of health care surfaces include surfaces of medicalor dental instruments, of medical or dental devices, of electronicapparatus employed for monitoring patient health, and of floors, walls,or fixtures of structures in which health care occurs. Health caresurfaces are found in hospital, surgical, infirmity, birthing, mortuary,and clinical diagnosis rooms. These surfaces can be those typified as“hard surfaces” (such as walls, floors, bed-pans, etc.,), or fabricsurfaces, e.g., knit, woven, and non-woven surfaces (such as surgicalgarments, draperies, bed linens, bandages, etc.,), or patient-careequipment (such as respirators, diagnostic equipment, shunts, bodyscopes, wheel chairs, beds, etc.,), or surgical and diagnosticequipment. Health care surfaces include articles and surfaces employedin animal health care.

As used herein, the term “instrument” refers to the various medical ordental instruments or devices that can benefit from cleaning with acomposition according to the present invention.

As used herein, the phrases “medical instrument,” “dental instrument,”“medical device,” “dental device,” “medical equipment,” or “dentalequipment” refer to instruments, devices, tools, appliances, apparatus,and equipment used in medicine or dentistry. Such instruments, devices,and equipment can be cold sterilized, soaked or washed and then heatsterilized, or otherwise benefit from cleaning in a composition of thepresent invention. These various instruments, devices and equipmentinclude, but are not limited to: diagnostic instruments, trays, pans,holders, racks, forceps, scissors, shears, saws (e.g. bone saws andtheir blades), hemostats, knives, chisels, rongeurs, files, nippers,drills, drill bits, rasps, burrs, spreaders, breakers, elevators,clamps, needle holders, carriers, clips, hooks, gouges, curettes,retractors, straightener, punches, extractors, scoops, keratomes,spatulas, expressors, trocars, dilators, cages, glassware, tubing,catheters, cannulas, plugs, stents, scopes (e.g., endoscopes,stethoscopes, and arthoscopes) and related equipment, and the like, orcombinations thereof.

As used herein, “agricultural” or “veterinary” objects or surfacesinclude animal feeds, animal watering stations and enclosures, animalquarters, animal veterinarian clinics (e.g. surgical or treatmentareas), animal surgical areas, and the like.

As used herein, the term “phosphorus-free” or “substantiallyphosphorus-free” refers to a composition, mixture, or ingredient thatdoes not contain phosphorus or a phosphorus-containing compound or towhich phosphorus or a phosphorus-containing compound has not been added.Should phosphorus or a phosphorus-containing compound be present throughcontamination of a phosphorus-free composition, mixture, or ingredients,the amount of phosphorus shall be less than 0.5 wt %. More preferably,the amount of phosphorus is less than 0.1 wt-%, and most preferably theamount of phosphorus is less than 0.01 wt %.

For the purpose of this patent application, successful microbialreduction is achieved when the microbial populations are reduced by atleast about 50%, or by significantly more than is achieved by a washwith water. Larger reductions in microbial population provide greaterlevels of protection.

As used herein, the term “sanitizer” refers to an agent that reduces thenumber of bacterial contaminants to safe levels as judged by publichealth requirements. In an embodiment, sanitizers for use in thisinvention will provide at least a 99.999% reduction (5-log orderreduction). These reductions can be evaluated using a procedure set outin Germicidal and Detergent Sanitizing Action of Disinfectants, OfficialMethods of Analysis of the Association of Official Analytical Chemists,paragraph 960.09 and applicable sections, 15th Edition, 1990 (EPAGuideline 91-2). According to this reference a sanitizer should providea 99.999% reduction (5-log order reduction) within 30 seconds at roomtemperature, 25±2° C., against several test organisms.

As used herein, the term “disinfectant” refers to an agent that killsall vegetative cells including most recognized pathogenicmicroorganisms, using the procedure described in A.O.A.C Use DilutionMethods, Official Methods of Analysis of the Association of OfficialAnalytical Chemists, paragraph 955.14 and applicable sections, 15thEdition, 1990 (EPA Guideline 91-2). As used herein, the term “high leveldisinfection” or “high level disinfectant” refers to a compound orcomposition that kills substantially all organisms, except high levelsof bacterial spores, and is effected with a chemical germicide clearedfor marketing as a sterilant by the Food and Drug Administration. Asused herein, the term “intermediate-level disinfection” or “intermediatelevel disinfectant” refers to a compound or composition that killsmycobacteria, most viruses, and bacteria with a chemical germicideregistered as a tuberculocide by the Environmental Protection Agency(EPA). As used herein, the term “low-level disinfection” or “low leveldisinfectant” refers to a compound or composition that kills someviruses and bacteria with a chemical germicide registered as a hospitaldisinfectant by the EPA.

As used in this invention, the term “sporicide” refers to a physical orchemical agent or process having the ability to cause greater than a 90%reduction (1-log order reduction) in the population of spores ofBacillus cereus or Bacillus subtilis within 10 seconds at 60° C. Incertain embodiments, the sporicidal compositions of the inventionprovide greater than a 99% reduction (2-log order reduction), greaterthan a 99.99% reduction (4-log order reduction), or greater than a99.999% reduction (5-log order reduction) in such population within 10seconds at 60° C.

Differentiation of antimicrobial “-cidal” or “-static” activity, thedefinitions which describe the degree of efficacy, and the officiallaboratory protocols for measuring this efficacy are considerations forunderstanding the relevance of antimicrobial agents and compositions.Antimicrobial compositions can affect two kinds of microbial celldamage. The first is a lethal, irreversible action resulting in completemicrobial cell destruction or incapacitation. The second type of celldamage is reversible, such that if the organism is rendered free of theagent, it can again multiply. The former is termed microbiocidal and thelater, microbistatic. A sanitizer and a disinfectant are, by definition,agents which provide antimicrobial or microbiocidal activity. Incontrast, a preservative is generally described as an inhibitor ormicrobistatic composition

As used herein, the term “alkyl” or “alkyl groups” refers to saturatedhydrocarbons having one or more carbon atoms, including straight-chainalkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl,octyl, nonyl, decyl, etc.), cyclic alkyl groups (or “cycloalkyl” or“alicyclic” or “carbocyclic” groups) (e.g., cyclopropyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, etc.), branched-chain alkyl groups(e.g., isopropyl, tert-butyl, sec-butyl, isobutyl, etc.), andalkyl-substituted alkyl groups (e.g., alkyl-substituted cycloalkylgroups and cycloalkyl-substituted alkyl groups).

Unless otherwise specified, the term “alkyl” includes both“unsubstituted alkyls” and “substituted alkyls.” As used herein, theterm “substituted alkyls” refers to alkyl groups having substituentsreplacing one or more hydrogens on one or more carbons of thehydrocarbon backbone. Such substituents may include, for example,alkenyl, alkynyl, halogeno, hydroxyl, alkylcarbonyloxy, arylcarbonyloxy,alkoxycarbonyloxy, aryloxy, aryloxycarbonyloxy, carboxylate,alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aminocarbonyl,alkylaminocarbonyl, dialkylaminocarbonyl, alkylthiocarbonyl, alkoxyl,phosphate, phosphonato, phosphinato, cyano, amino (including alkylamino, dialkylamino, arylamino, diarylamino, and alkylarylamino),acylamino (including alkylcarbonylamino, arylcarbonylamino, carbamoyland ureido), imino, sulfhydryl, alkylthio, arylthio, thiocarboxylate,sulfates, alkylsulfinyl, sulfonates, sulfamoyl, sulfonamido, nitro,trifluoromethyl, cyano, azido, heterocyclic, alkylaryl, or aromatic(including heteroaromatic) groups.

In some embodiments, substituted alkyls can include a heterocyclicgroup. As used herein, the term “heterocyclic group” includes closedring structures analogous to carbocyclic groups in which one or more ofthe carbon atoms in the ring is an element other than carbon, forexample, nitrogen, sulfur or oxygen. Heterocyclic groups may besaturated or unsaturated. Exemplary heterocyclic groups include, but arenot limited to, aziridine, ethylene oxide (epoxides, oxiranes), thiirane(episulfides), dioxirane, azetidine, oxetane, thietane, dioxetane,dithietane, dithiete, azolidine, pyrrolidine, pyrroline, oxolane,dihydrofuran, and furan.

Compounds of the Invention

The present invention relates, at least in part, tosulfoperoxycarboxylic acids, compositions thereof, and the use thereofin a variety of bleaching, disinfecting and cleaning applications. Thesulfoperoxycarboxylic acids of the present invention are also useful ascoupling agents. Further, certain compounds of the present invention canbe derived from non-petroleum based, renewable oils, e.g., castor, toll,soybean, canola, olive, peanut, tallow, rapeseed, and palm oils.

As used herein, the term “sulfoperoxycarboxylic acid,” “sulfonatedperacid,” or “sulfonated peroxycarboxylic acid” refers to theperoxycarboxylic acid form of a sulfonated carboxylic acid. In someembodiments, the sulfonated peracids of the present invention aremid-chain sulfonated peracids. As used herein, the term “mid-chainsulfonated peracid” refers to a peracid compound that includes asulfonate group attached to a carbon that is at least one carbon (e.g.,the three position or further) from the carbon of the percarboxylic acidgroup in the carbon backbone of the percarboxylic acid chain, whereinthe at least one carbon is not in the terminal position. As used herein,the term “terminal position,” refers to the carbon on the carbonbackbone chain of a percarboxylic acid that is furthest from thepercarboxyl group.

Without wishing to be bound by any particular theory, it is thought thatmid-chain sulfonated peracids, e.g., mid-chain sulfonated peracids witha C10-C18 carbon backbone have a substantially greater solubilitycompared to terminally sulfonated peracids of a similar chain length,even at an acidic pH. For example, at a pH of 4, the terminallysulfonated peracid, 11-sulfoundecane peroxoic acid has a relatively lowsolubility of about 1.3%. At the same pH, the mid chain sulfonatedperacid, persulfonated oleic acid has a solubility of greater than about50%. This is unexpected as an increase in peracid chain length isthought to lead to a decrease in solubility. The issue of low solubilitywhen using long chain peracids has been addressed by increasing the pHto above 7. However, at increased pH antimicrobial efficacy issubstantially reduced. Further, bleaching efficacy decreasesproportionally with every pH unit increase over about 7. Thus,solubility at an acidic pH (lower than about 7) is beneficial to themid-chain sulfonated peracids of the present invention.

The sulfoperoxycarboxylic acids of the present invention can be usedalone, or can be combined with additional ingredients. In someembodiments, compositions of the present invention can include one ormore of the sulfoperoxycarboxylic acids of the present invention.

Peroxycarboxylic (or percarboxylic) acids generally have the formulaR(CO₃H)_(n), where, for example, R is an alkyl, arylalkyl, cycloalkyl,aromatic, or heterocyclic group, and n is one, two, or three, and namedby prefixing the parent acid with peroxy. Percarboxylic acids can bemade by the direct, acid catalyzed equilibrium action of hydrogenperoxide with the carboxylic acid, by autooxidation of aldehydes, orfrom acid chlorides, and hydrides, or carboxylic anhydrides withhydrogen or sodium peroxide. The R group can be saturated or unsaturatedas well as substituted or unsubstituted.

The chemical structures herein are drawn according to the conventionalstandards known in the art. Thus, where an atom, such as a carbon atom,as drawn appears to have an unsatisfied valency, then that valency isassumed to be satisfied by a hydrogen atom, even though that hydrogenatom is not necessarily explicitly drawn. The structures of some of thecompounds of this invention include stereogenic carbon atoms. It is tobe understood that isomers arising from such asymmetry (e.g., allenantiomers and diastereomers) are included within the scope of thisinvention unless indicated otherwise. That is, unless otherwisestipulated, any chiral carbon center may be of either (R)- or(S)-stereochemistry. Such isomers can be obtained in substantially pureform by classical separation techniques and bystereochemically-controlled synthesis. Furthermore, alkenes can includeeither the E- or Z-geometry, where appropriate. In addition, thecompounds of the present invention may exist in unsolvated as well assolvated forms with acceptable solvents such as water, THF, ethanol, andthe like. In general, the solvated forms are considered equivalent tothe unsolvated forms for the purposes of the present invention.

In some aspects, the present invention pertains to sulfoperoxycarboxylicacids of Formula I:

wherein R₁ is hydrogen, or a substituted or unsubstituted alkyl group;

R₂ is a substituted or unsubstituted alkyl group;

X is hydrogen, a cationic group, or an ester forming moiety;

or salts or esters thereof.

In some embodiments, R₁ is a substituted or unsubstituted C_(m) alkylgroup; X is hydrogen a cationic group, or an ester forming moiety; R₂ isa substituted or unsubstituted C_(n) alkyl group; m=1 to 10; n=1 to 10;and m+n is less than 18, or salts, esters or mixtures thereof.

In some embodiments, R₁ is hydrogen. In other embodiments, R₁ is asubstituted or unsubstituted alkyl group. In some embodiments, R₁ is asubstituted or unsubstituted alkyl group that does not include a cyclicalkyl group. In some embodiments, R₁ is a substituted alkyl group. Insome embodiments, R₁ is an unsubstituted C₁-C₉ alkyl group. In someembodiments, R₁ is an unsubstituted C₇ or C₈ alkyl. In otherembodiments, R₁ is a substituted C₈-C₁₀ alkyl group. In someembodiments, R₁ is a substituted C₈-C₁₀ alkyl group is substituted withat least 1, or at least 2 hydroxyl groups. In still yet otherembodiments, R₁ is a substituted C₁-C₉ alkyl group. In some embodiments,R₁ is a substituted C₁-C₉ substituted alkyl group is substituted with atleast 1 SO₃H group.

In other embodiments, R₁ is a C₉-C₁₀ substituted alkyl group. In someembodiments, R₁ is a substituted C₉-C₁₀ alkyl group wherein at least twoof the carbons on the carbon backbone form a heterocyclic group. In someembodiments, the heterocyclic group is an epoxide group.

In some embodiments, R₂ is a substituted C₁ to C₁₀ alkyl group. In someembodiments, R₂ is a substituted C₈-C₁₀ alkyl. In some embodiments, R₂is an unsubstituted C₆-C₉ alkyl. In other embodiments, R₂ is a C₈ to C₁₀alkyl group substituted with at least one hydroxyl group. In someembodiments, R₂ is a C₁₀ alkyl group substituted with at least twohydroxyl groups. In other embodiments, R₂ is a C₈ alkyl groupsubstituted with at least one SO₃H group. In some embodiments, R₂ is asubstituted C₉ group, wherein at least two of the carbons on the carbonbackbone form a heterocyclic group. In some embodiments, theheterocyclic group is an epoxide group. In some embodiments, R₁ is aC₈-C₉ substituted or unsubstituted alkyl, and R₂ is a C₇-C₈ substitutedor unsubstituted alkyl.

In some embodiments, the compound of the invention is selected from thegroup consisting of:

salts, esters, and mixtures and derivatives thereof.

In other embodiments, the compound of the invention is selected from thegroup consisting of:

and mixtures and derivatives thereof.

Compounds of the invention are also shown in Table 1 below.

TABLE 1 Sulfonated Peroxyacid Compounds ID Structure/Name of Compound A

10-Hydroxy-9-sulfooctadecaneperoxoic acid B

9,10-Dihydroxy-8-sulfooctadecaneperoxoic acid C

9-Sulfooctadecaneperoxoic acid D

11-Sulfoundecaneperoxoic acid E

10,11-Disulfoundecaneperoxoic acid F

8-(3-octyloxiran-2-yl)-8-sulfooctaneperoxoic acid G

9,10-Dihydroxy-11-sulfooctadecaneperoxoic acid H

8-(3-octyloxiran-2-yl)-8-sulfooctaneperoxoic acid I

9-Hydroxy-10-sulfooctadecaneperoxoic acid J

10-Sulfooctadecaneperoxoic acid K

9,10-Disulfooctadecaneperoxoic acid L

10-Sulfoundecaneperoxoic acid M

9-(3-heptyloxiran-2-yl)-9-sulfononaneperoxoic acid N

10,11-dihydroxy-9-sulfooctadecaneperoxoic acid O

8,9-dihydroxy-10-sulfooctadecaneperoxoic acid

In some embodiments, the starting material for the preparation of thecompounds of the present invention is a sulfonated fatty acid. Withoutwishing to be bound by any particular theory, it is thought that thesulfo-group is inert in an oxidative environment. Further, it is thoughtthat the hydrophility of the sulfo-group is not as impacted by pH asother substituents. In some embodiments, the sulfonated percarboxylicacids of the present invention are formed from commercially availablesulfonated fatty acids. In other embodiments, the compounds of thepresent invention are formed from commercially available non-sulfonatedfatty acids, which can be sulfonated. In some embodiments, the startingfatty acid will be sulfonated prior to conversion to a peroxycarboxylicacid. In other embodiments, the starting fatty acid will be sulfonatedat the same time or after the formation of the peroxycarboxylic acid.Sulfonated fatty acids suitable for use in forming compounds of thepresent invention include, but are not limited to, 11-sulfoundecanoicacid, 10,11-disulfoundecanoic acid, sulfonated oleic acid, sulfonatedlinoleic acid, sulfonated palmitoleic acid and sulfonated stearic acid.

Without wishing to be bound by any particular theory, it is thought thatthe peracid formed from certain commercially available sulfonated oleicacid starting materials includes a mixture of the compounds of thepresent invention. It is thought that this is due, in part, to thenature of the sulfonated oleic acid starting material. That is, it isthought that because the sulfonated oleic acid starting material isderived from naturally occurring sources, it is not chemically pure,i.e., does not contain only one form of the sulfonated oleic acid. Thus,without wishing to be bound by any particular theory it is thought thatsulfonated peroleic acid formed (hereinafter referred to as the“sulfonated peroleic acid product”) can include a mixture of CompoundsA, N, I, and O as the primary components. Without wishing to be bound byany particular theory it is thought that in some embodiments, thesulfonated peroleic acid product includes about 20-25 wt % Compound A(10-Hydroxy-9-sulfooctadecaneperoxoic acid) about 20-25 wt % Compound N(10,11-dihydroxy-9-sulfooctadecaneperoxoic acid), about 20-25 wt %Compound I (9-Hydroxy-10-sulfooctadecaneperoxoic acid), and about 20-25wt % Compound O (8,9-dihydroxy-10-sulfooctadecaneperoxoic acid). Theremainder of the product is thought to include about 5 to about 10 wt %of a mixture of these compounds.

The sulfoperoxyacids can be formed using a variety of reactionmechanisms. For example, in some embodiments, the peracids are formed bythe direct acid catalyzed equilibrium action of hydrogen peroxide withthe starting materials.

In some embodiments, the sulfonated carboxylic acids for use in formingthe compounds of the present invention are not sulfonated at the aposition. As used herein, the term “a position” refers to the carbon onthe carbon backbone of the percarboxylic acid chain that is directlyconnected to, viz. immediately next to, the carboxylic acid group. Ithas been found that having the sulfonate group at the a position of thefatty acid prohibits the oxidation and/or perhydrolysis of thecarboxylic acid group to form the corresponding peroxycarboxylic acid.Without wishing to be bound by any particular theory, it is thought thatthe α-sulfo group makes the carboxylic acid group on the fatty acidelectronically deficient, and thus oxidation and/or perhydrolysis andformation of the corresponding percarboxylic acid requires extremely lowpHs. Upon neutralization or even moderate elevation of these pHs, it isthought that the peracids very rapidly hydrolyze back to the parentacids, rendering them impractical for most applications.

Sulfonated Peroxycarboxylic Acid Compositions

In some aspects, the present invention relates to compositions includinga sulfonated peroxycarboxylic acid compound, or mixture thereof, ofFormula I. The compositions of the present invention can be used asbleaching compositions for a variety of substrates and surfaces, e.g.,textiles, hard surfaces. The compositions of the present invention canalso be used as disinfectant or antimicrobial compositions. Further,compounds of the present invention can be used as coupling agents incompositions for various applications, e.g., food contact sanitizing,hard surface disinfection, textile disinfection. In some embodiments,compositions containing compounds of the present invention can bemultipurpose. That is, the compositions of the present invention can,for example, act as both antimicrobials and bleaches, or as bothcoupling agents, and bleaching agents.

The compositions of the present invention also show enhanced stabilitycompared to conventional peroxygen containing compositions. In someembodiments, the compositions of the present invention are stable for atleast about 1 year at room temperature. In some embodiments, thecompositions of the present invention are stable at about 100° F. for atleast 30 days. In other embodiments, the compositions of the presentinvention are stable at about 140° F. for at least 30 days. For example,11-sulfoundecanoic peroxyacid (Compound D) is stable as a powder systemat about 140° F. for at least 30 days.

The compositions of the present invention have no or low odor. Forexample, in some embodiments, compositions of the present invention havean odor less unpleasant than (e.g., as measured by an hedonic tonerating) than 5, 4, 3, 2, or 1 wt-% acetic acid in water. In otherembodiments, the compositions of the present invention have no odordetectable by a user.

In some embodiments, the compositions of the present invention include asulfonated peracid or mixture thereof of Formula I, and at least oneadditional ingredient. Additional ingredients suitable for use with thecompositions of the present invention include, but are not limited to,oxidizing agents, carboxylic acids, surfactants, stabilizing agents(e.g., metal chelators), and mixtures thereof. The compounds andcompositions of the invention can also be used in conjunction withconventional cleaning agents, e.g., alkaline detergents.

In some embodiments, the compositions of the present invention can beused as a sanitizing composition for articles cleaned using a clean inplace (CIP) technique. Such compositions can include an oxidizing agent,a stabilizing agent, an acidulant and a surfactant or mixture thereof,in the following concentrations.

TABLE A Concentrate CIP Sanitizer by Weight % Oxidizing Agent 0.1-10 2-85-7 Stabilizing Agent 0.1-10 0.5-5   1-2 Acidulant   0-50 10-40 20-30Surfactant   0-50 10-40 25-35

In other embodiments, the compositions of the present invention can beused as a textile disinfectant/sanitizer. Such compositions can includeoxidizing agent, stabilizing agent and a carboxylic acid in thefollowing concentrations.

TABLE B Concentrate Textile Disinfectant/Sanitizer by Weight % OxidizingAgent 10-75 25-60 30-50 Stabilizing Agent 0.1-10  0.5-5   2-4 CarboxylicAcid  1-40 10-30 20-25

Oxidizing Agents

In some aspects, the compositions of the present invention include acompound of Formula I. In some embodiments, the compositions of thepresent invention further include at least one oxidizing agent. In someembodiments, the compositions of the present invention are substantiallyfree of an oxidizing agent. When present, the present composition caninclude any of a variety of oxidizing agents, for example, hydrogenperoxide. The oxidizing agent can be present at an amount effective toconvert a sulfonated carboxylic acid to a sulfonated peroxycarboxylicacid. In some embodiments, the oxidizing agent can also haveantimicrobial activity. In other embodiments, the oxidizing agent ispresent in an amount insufficient to exhibit antimicrobial activity.

In some embodiments, the compositions of the present invention includeabout 0.001 wt % oxidizing agent to about 99 wt % oxidizing agent. Inother embodiments, the compositions of the present invention includeabout 1 wt % to about 60 wt % oxidizing agent. In some embodiments, thecompositions of the invention include about 50 wt % to about 80 wt %oxidizing agent. In other embodiments, the compositions of the inventioninclude about 15 wt % to about 30 wt % oxidizing agent. In yet otherembodiments, the compositions of the present invention include about 25wt % oxidizing agent. It is to be understood that all ranges and valuesbetween these ranges and values are encompassed by the presentinvention.

Examples of inorganic oxidizing agents include the following types ofcompounds or sources of these compounds, or alkali metal salts includingthese types of compounds, or forming an adduct therewith: hydrogenperoxide, urea-hydrogen peroxide complexes or hydrogen peroxide donorsof: group 1 (IA) oxidizing agents, for example lithium peroxide, sodiumperoxide; group 2 (IIA) oxidizing agents, for example magnesiumperoxide, calcium peroxide, strontium peroxide, barium peroxide; group12 (IIB) oxidizing agents, for example zinc peroxide; group 13 (IIIA)oxidizing agents, for example boron compounds, such as perborates, forexample sodium perborate hexahydrate of the formulaNa₂[B₂(O₂)₂(OH)₄].6H₂O (also called sodium perborate tetrahydrate);sodium peroxyborate tetrahydrate of the formula Na₂B₂(O₂)₂[(OH)₄].4H₂O(also called sodium perborate trihydrate); sodium peroxyborate of theformula Na₂[B₂(O₂)₂(OH)₄] (also called sodium perborate monohydrate);group 14 (IVA) oxidizing agents, for example persilicates andperoxycarbonates, which are also called percarbonates, such aspersilicates or peroxycarbonates of alkali metals; group 15 (VA)oxidizing agents, for example peroxynitrous acid and its salts;peroxyphosphoric acids and their salts, for example, perphosphates;group 16 (VIA) oxidizing agents, for example peroxysulfuric acids andtheir salts, such as peroxymonosulfuric and peroxydisulfuric acids, andtheir salts, such as persulfates, for example, sodium persulfate; andgroup VIIa oxidizing agents such as sodium periodate, potassiumperchlorate. Other active inorganic oxygen compounds can includetransition metal peroxides; and other such peroxygen compounds, andmixtures thereof.

In some embodiments, the compositions of the present invention employone or more of the inorganic oxidizing agents listed above. Suitableinorganic oxidizing agents include ozone, hydrogen peroxide, hydrogenperoxide adduct, group IIIA oxidizing agent, or hydrogen peroxide donorsof group VIA oxidizing agent, group VA oxidizing agent, group VIIAoxidizing agent, or mixtures thereof. Suitable examples of suchinorganic oxidizing agents include percarbonate, perborate, persulfate,perphosphate, persilicate, or mixtures thereof.

Carboxylic and Percarboxylic Acids In some embodiments, the compositionsof the present invention include at least one sulfoperoxycarboxylic acidof the present invention, and at least one carboxylic and/orpercarboxylic acid. In some embodiments, the compositions of the presentinvention include at least two, at least three, or at least four or morecarboxylic and/or percarboxylic acids.

In some embodiments, the carboxylic acid for use with the compositionsof the present invention includes a C₁ to C₂₂ carboxylic acid. In someembodiments, the carboxylic acid for use with the compositions of thepresent invention is a C₅ to C₁₁ carboxylic acid. In some embodiments,the carboxylic acid for use with the compositions of the presentinvention is a C₁ to C₄ carboxylic acid. Examples of suitable carboxylicacids include, but are not limited to, formic, acetic, propionic,butanoic, pentanoic, hexanoic, heptanoic, octanoic, nonanoic, decanoic,undecanoic, dodecanoic, as well as their branched isomers, lactic,maleic, ascorbic, citric, hydroxyacetic, neopentanoic, neoheptanoic,neodecanoic, oxalic, malonic, succinic, glutaric, adipic, pimelic subricacid, and mixtures thereof.

In some embodiments, the compositions of the present invention includeabout 0.1 wt % to about 80 wt % of a carboxylic acid. In otherembodiments, the compositions of the present invention include about 1wt % to about 60 wt % of a carboxylic acid. In yet other embodiments,the compositions of the present invention include about 20 wt %, about30 wt %, or about 40 wt % of a carboxylic acid. In some embodiments, thecompositions of the present invention include about 5 wt % to about 10wt % of acetic acid. In other embodiments, the compositions of thepresent invention include about 5 wt % to about 10 wt % of octanoicacid. In other embodiments, the compositions of the present inventioninclude a combination of octanoic acid and acetic acid.

In some embodiments, the compositions of the present invention include acompound of Formula I, and at least one peroxycarboxylic acid.Peroxycarboxylic acids useful in the compositions and methods of thepresent invention include peroxyformic, peroxyacetic, peroxypropionic,peroxybutanoic, peroxypentanoic, peroxyhexanoic, peroxyheptanoic,peroxyoctanoic, peroxynonanoic, peroxydecanoic, peroxyundecanoic,peroxydodecanoic, or the peroxyacids of their branched chain isomers,peroxylactic, peroxymaleic, peroxyascorbic, peroxyhydroxyacetic,peroxyoxalic, peroxymalonic, peroxysuccinic, peroxyglutaric,peroxyadipic, peroxypimelic and peroxysubric acid and mixtures thereof.In some embodiments, the compositions of the invention utilize acombination of several different peroxycarboxylic acids. For example, insome embodiments, the composition includes one or more C₁ to C₄peroxycarboxylic acids and one or more C₅ to C₁₁ peroxycarboxylic acids.In some embodiments, the C₁ to C₄ peroxycarboxylic acid is peroxyaceticacid and the C₅ to C₁₁ acid is peroxyoctanoic acid.

In some embodiments, the compositions of the present invention includeperoxyacetic acid. Peroxyacetic (or peracetic) acid is aperoxycarboxylic acid having the formula: CH₃COOOH. Generally,peroxyacetic acid is a liquid having an acrid odor at higherconcentrations and is freely soluble in water, alcohol, ether, andsulfuric acid. Peroxyacetic acid can be prepared through any number ofmethods known to those of skill in the art including preparation fromacetaldehyde and oxygen in the presence of cobalt acetate. A solution ofperoxyacetic acid can be obtained by combining acetic acid with hydrogenperoxide. A 50% solution of peroxyacetic acid can be obtained bycombining acetic anhydride, hydrogen peroxide and sulfuric acid.

In some embodiments, the compositions of the present invention includeperoxyoctanoic acid, peroxynonanoic acid, or peroxyheptanoic acid Insome embodiments, the compositions include peroxyoctanoic acid.Peroxyoctanoic (or peroctanoic) acid is a peroxycarboxylic acid havingthe formula, for example, of n-peroxyoctanoic acid: CH₃(CH₂)₆COOOH.Peroxyoctanoic acid can be an acid with a straight chain alkyl moiety,an acid with a branched alkyl moiety, or a mixture thereof.Peroxyoctanoic acid can be prepared through any number of methods knownto those of skill in the art. A solution of peroxyoctanoic acid can beobtained by combining octanoic acid and hydrogen peroxide and ahydrotrope, solvent or carrier.

In some embodiments, the compositions of the present invention includeabout 0.1 wt % to about 90 wt % of one or more peroxycarboxylic acids.In other embodiments, the compositions of the present invention includeabout 1 wt % to about 25 wt % of one or more peroxycarboxylic acids. Inyet other embodiments, the compositions of the present invention includeabout 5 wt % to about 10 wt % of one or more peroxycarboxylic acids. Insome embodiments, the compositions of the present invention includeabout 1 wt % to about 25 wt % of peroxyacetic acid. In otherembodiments, the compositions of the present invention include about 0.1wt % to about 10 wt % of peroxyoctanoic acid. In still yet otherembodiments, the compositions of the present invention include a mixtureof about 5 wt % peroxyacetic acid, and about 1.5 wt % peroxyoctanoicacid.

Surfactants

In some embodiments, the compositions of the present invention include asurfactant. Surfactants suitable for use with the compositions of thepresent invention include, but are not limited to, nonionic surfactants,anionic surfactants, and zwitterionic surfactants. In some embodiments,the compositions of the present invention include about 10 wt % to about50 wt % of a surfactant. In other embodiments the compositions of thepresent invention include about 15 wt % to about 30% of a surfactant. Instill yet other embodiments, the compositions of the present inventioninclude about 25 wt % of a surfactant. In some embodiments, thecompositions of the present invention include about 100 ppm to about1000 ppm of a surfactant.

Nonionic Surfactants

Suitable nonionic surfactants suitable for use with the compositions ofthe present invention include alkoxylated surfactants. Suitablealkoxylated surfactants include EO/PO copolymers, capped EO/POcopolymers, alcohol alkoxylates, capped alcohol alkoxylates, mixturesthereof, or the like. Suitable alkoxylated surfactants for use assolvents include EO/PO block copolymers, such as the Pluronic andreverse Pluronic surfactants; alcohol alkoxylates, such as Dehypon LS-54(R-(EO)₅(PO)₄) and Dehypon LS-36 (R-(EO)₃(PO)₆); and capped alcoholalkoxylates, such as Plurafac LF221 and Tegoten EC11; mixtures thereof,or the like.

Semi-Polar Nonionic Surfactants

The semi-polar type of nonionic surface active agents are another classof nonionic surfactant useful in compositions of the present invention.Semi-polar nonionic surfactants include the amine oxides, phosphineoxides, sulfoxides and their alkoxylated derivatives.

Amine oxides are tertiary amine oxides corresponding to the generalformula:

wherein the arrow is a conventional representation of a semi-polar bond;and, R¹, R², and R³ may be aliphatic, aromatic, heterocyclic, alicyclic,or combinations thereof Generally, for amine oxides of detergentinterest, R¹ is an alkyl radical of from about 8 to about 24 carbonatoms; R² and R³ are alkyl or hydroxyalkyl of 1-3 carbon atoms or amixture thereof; R² and R³ can be attached to each other, e.g. throughan oxygen or nitrogen atom, to form a ring structure; R⁴ is an alkyleneor a hydroxyalkylene group containing 2 to 3 carbon atoms; and n rangesfrom 0 to about 20. An amine oxide can be generated from thecorresponding amine and an oxidizing agent, such as hydrogen peroxide.

Useful water soluble amine oxide surfactants are selected from theoctyl, decyl, dodecyl, isododecyl, coconut, or tallow alkyl di-(loweralkyl)amine oxides, specific examples of which are octyldimethylamineoxide, nonyldimethylamine oxide, decyldimethylamine oxide,undecyldimethylamine oxide, dodecyldimethylamine oxide,iso-dodecyldimethyl amine oxide, tridecyldimethylamine oxide,tetradecyldimethylamine oxide, pentadecyldimethylamine oxide,hexadecyldimethylamine oxide, heptadecyldimethylamine oxide,octadecyldimethylaine oxide, dodecyldipropylamine oxide,tetradecyldipropylamine oxide, hexadecyldipropylamine oxide,tetradecyldibutylamine oxide, octadecyldibutylamine oxide,bis(2-hydroxyethyl)dodecylamine oxide,bis(2-hydroxyethyl)-3-dodecoxy-1-hydroxypropylamine oxide,dimethyl-(2-hydroxydodecyl)amine oxide, 3,6,9-trioctadecyldimethylamineoxide and 3-dodecoxy-2-hydroxypropyldi-(2-hydroxyethyl)amine oxide.

Anionic Surfactants

Anionic sulfate surfactants suitable for use in the present compositionsinclude alkyl ether sulfates, alkyl sulfates, the linear and branchedprimary and secondary alkyl sulfates, alkyl ethoxysulfates, fatty oleylglycerol sulfates, alkyl phenol ethylene oxide ether sulfates, theC₅-C₁₇ acyl-N—(C₁-C₄ alkyl) and —N—(C₁-C₂ hydroxyalkyl)glucaminesulfates, and sulfates of alkylpolysaccharides such as the sulfates ofalkylpolyglucoside, and the like. Also included are the alkyl sulfates,alkyl poly(ethyleneoxy)ether sulfates and aromaticpoly(ethyleneoxy)sulfates such as the sulfates or condensation productsof ethylene oxide and nonyl phenol (usually having 1 to 6 oxyethylenegroups per molecule).

Anionic sulfonate surfactants suitable for use in the presentcompositions also include alkyl sulfonates, the linear and branchedprimary and secondary alkyl sulfonates, and the aromatic sulfonates withor without substituents.

Anionic carboxylate surfactants suitable for use in the presentcompositions include carboxylic acids (and salts), such as alkanoicacids (and alkanoates), ester carboxylic acids (e.g. alkyl succinates),ether carboxylic acids, and the like. Such carboxylates include alkylethoxy carboxylates, alkyl aryl ethoxy carboxylates, alkyl polyethoxypolycarboxylate surfactants and soaps (e.g. alkyl carboxyls). Secondarycarboxylates useful in the present compositions include those whichcontain a carboxyl unit connected to a secondary carbon. The secondarycarbon can be in a ring structure, e.g. as in p-octyl benzoic acid, oras in alkyl-substituted cyclohexyl carboxylates. The secondarycarboxylate surfactants typically contain no ether linkages, no esterlinkages and no hydroxyl groups. Further, they typically lack nitrogenatoms in the head-group (amphiphilic portion). Suitable secondary soapsurfactants typically contain 11-13 total carbon atoms, although morecarbons atoms (e.g., up to 16) can be present. Suitable carboxylatesalso include acylamino acids (and salts), such as acylgluamates, acylpeptides, sarcosinates (e.g. N-acyl sarcosinates), taurates (e.g. N-acyltaurates and fatty acid amides of methyl tauride), and the like.

Suitable anionic surfactants include alkyl or alkylaryl ethoxycarboxylates of the following formula:

R—O—(CH₂CH₂O)_(n)(CH₂)_(m)—CO₂X   (3)

in which R is a C₈ to C₂₂ alkyl group or

in which R¹ is a C₄-C₁₆ alkyl group; n is an integer of 1-20; m is aninteger of 1-3; and X is a counter ion, such as hydrogen, sodium,potassium, lithium, ammonium, or an amine salt such as monoethanolamine,diethanolamine or triethanolamine. In some embodiments, n is an integerof 4 to 10 and m is 1. In some embodiments, R is a C₈-C₁₆ alkyl group.In some embodiments, R is a C₁₂-C₁₄ alkyl group, n is 4, and m is 1.

In other embodiments, R is

and R¹ is a C₆-C₁₂ alkyl group. In still yet other embodiments, R¹ is aC₉ alkyl group, n is 10 and m is 1.

Such alkyl and alkylaryl ethoxy carboxylates are commercially available.These ethoxy carboxylates are typically available as the acid forms,which can be readily converted to the anionic or salt form. Commerciallyavailable carboxylates include, Neodox 23-4, a C₁₂₋₁₃ alkyl polyethoxy(4) carboxylic acid (Shell Chemical), and Emcol CNP-110, a C₉ alkylarylpolyethoxy (10) carboxylic acid (Witco Chemical). Carboxylates are alsoavailable from Clariant, e.g. the product Sandopan® DTC, a C₁₃ alkylpolyethoxy (7) carboxylic acid.

Amphoteric Surfactants

Amphoteric, or ampholytic, surfactants contain both a basic and anacidic hydrophilic group and an organic hydrophobic group. These ionicentities may be any of anionic or cationic groups described herein forother types of surfactants. A basic nitrogen and an acidic carboxylategroup are the typical functional groups employed as the basic and acidichydrophilic groups. In a few surfactants, sulfonate, sulfate,phosphonate or phosphate provide the negative charge.

Amphoteric surfactants can be broadly described as derivatives ofaliphatic secondary and tertiary amines, in which the aliphatic radicalmay be straight chain or branched and wherein one of the aliphaticsubstituents contains from about 8 to 18 carbon atoms and one containsan anionic water solubilizing group, e.g., carboxy, sulfo, sulfato,phosphate, or phosphono. Amphoteric surfactants are subdivided into twomajor classes known to those of skill in the art and described in“Surfactant Encyclopedia” Cosmetics & Toiletries, Vol. 104 (2) 69-71(1989). The first class includes acyl/dialkyl ethylenediaminederivatives (e.g. 2-alkyl hydroxyethyl imidazoline derivatives) andtheir salts. The second class includes N-alkylamino acids and theirsalts. Some amphoteric surfactants can be envisioned as fitting intoboth classes.

Amphoteric surfactants can be synthesized by methods known to those ofskill in the art. For example, 2-alkyl hydroxyethyl imidazoline issynthesized by condensation and ring closure of a long chain carboxylicacid (or a derivative) with dialkyl ethylenediamine. Commercialamphoteric surfactants are derivatized by subsequent hydrolysis andring-opening of the imidazoline ring by alkylation—for example withchloroacetic acid or ethyl acetate. During alkylation, one or twocarboxy-alkyl groups react to form a tertiary amine and an ether linkagewith differing alkylating agents yielding different tertiary amines.

Long chain imidazole derivatives having application in the presentinvention generally have the general formula:

wherein R is an acyclic hydrophobic group containing from about 8 to 18carbon atoms and M is a cation to neutralize the charge of the anion,generally sodium. Commercially prominent imidazoline-derived amphotericsthat can be employed in the present compositions include for example:Cocoamphopropionate, Cocoamphocarboxy-propionate, Cocoamphoglycinate,Cocoamphocarboxy-glycinate, Cocoamphopropyl-sulfonate, andCocoamphocarboxy-propionic acid. Amphocarboxylic acids can be producedfrom fatty imidazolines in which the dicarboxylic acid functionality ofthe amphodicarboxylic acid is diacetic acid and/or dipropionic acid.

The carboxymethylated compounds (glycinates) described herein abovefrequently are called betaines. Betaines are a special class ofamphoteric discussed herein below in the section entitled, ZwitterionSurfactants.

Long chain N-alkylamino acids are readily prepared by reaction RNH₂, inwhich R═C₈-C₁₈ straight or branched chain alkyl, fatty amines withhalogenated carboxylic acids. Alkylation of the primary amino groups ofan amino acid leads to secondary and tertiary amines. Alkyl substituentsmay have additional amino groups that provide more than one reactivenitrogen center. Most commercial N-alkylamine acids are alkylderivatives of beta-alanine or beta-N(2-carboxyethyl)alanine. Examplesof commercial N-alkylamino acid ampholytes having application in thisinvention include alkyl beta-amino dipropionates, RN(C₂H₄COOM)₂ andRNHC₂H₄COOM. In an embodiment, R can be an acyclic hydrophobic groupcontaining from about 8 to about 18 carbon atoms, and M is a cation toneutralize the charge of the anion.

Suitable amphoteric surfactants include those derived from coconutproducts such as coconut oil or coconut fatty acid. Additional suitablecoconut derived surfactants include as part of their structure anethylenediamine moiety, an alkanolamide moiety, an amino acid moiety,e.g., glycine, or a combination thereof; and an aliphatic substituent offrom about 8 to 18 (e.g., 12) carbon atoms. Such a surfactant can alsobe considered an alkyl amphodicarboxylic acid. These amphotericsurfactants can include chemical structures represented as:C₁₂-alkyl-C(O)—NH—CH₂—CH₂—N⁺(CH₂—CH₂—CO₂Na)₂—CH₂—CH₂—OH orC₁₂-alkyl-C(O)—N(H)—CH₂—CH₂—N⁺(CH₂—CO₂Na)₂—CH₂—CH₂—OH. Disodiumcocoampho dipropionate is one suitable amphoteric surfactant and iscommercially available under the tradename Miranol™ FBS from RhodiaInc., Cranbury, N.J. Another suitable coconut derived amphotericsurfactant with the chemical name disodium cocoampho diacetate is soldunder the tradename Mirataine™ JCHA, also from Rhodia Inc., Cranbury,N.J.

A typical listing of amphoteric classes, and species of thesesurfactants, is given in U.S. Pat. No. 3,929,678 issued to Laughlin andHeuring on Dec. 30, 1975. Further examples are given in “Surface ActiveAgents and Detergents” (Vol. I and II by Schwartz, Perry and Berch).

Zwitterionic Surfactants

Zwitterionic surfactants can be thought of as a subset of the amphotericsurfactants and can include an anionic charge. Zwitterionic surfactantscan be broadly described as derivatives of secondary and tertiaryamines, derivatives of heterocyclic secondary and tertiary amines, orderivatives of quaternary ammonium, quaternary phosphonium or tertiarysulfonium compounds. Typically, a zwitterionic surfactant includes apositive charged quaternary ammonium or, in some cases, a sulfonium orphosphonium ion; a negative charged carboxyl group; and an alkyl group.Zwitterionics generally contain cationic and anionic groups which ionizeto a nearly equal degree in the isoelectric region of the molecule andwhich can develop strong“inner-salt” attraction betweenpositive-negative charge centers. Examples of such zwitterionicsynthetic surfactants include derivatives of aliphatic quaternaryammonium, phosphonium, and sulfonium compounds, in which the aliphaticradicals can be straight chain or branched, and wherein one of thealiphatic substituents contains from 8 to 18 carbon atoms and onecontains an anionic water solubilizing group, e.g., carboxy, sulfonate,sulfate, phosphate, or phosphonate. Betaine and sultaine surfactants areexemplary zwitterionic surfactants for use herein.

A general formula for these compounds is:

wherein R¹ contains an alkyl, alkenyl, or hydroxyalkyl radical of from 8to 18 carbon atoms having from 0 to 10 ethylene oxide moieties and from0 to 1 glyceryl moiety; Y is selected from the group consisting ofnitrogen, phosphorus, and sulfur atoms; R² is an alkyl or monohydroxyalkyl group containing 1 to 3 carbon atoms; x is 1 when Y is a sulfuratom and 2 when Y is a nitrogen or phosphorus atom, R³ is an alkylene orhydroxy alkylene or hydroxy alkylene of from 1 to 4 carbon atoms and Zis a radical selected from the group consisting of carboxylate,sulfonate, sulfate, phosphonate, and phosphate groups.

Examples of zwitterionic surfactants having the structures listed aboveinclude:4-[N,N-di(2-hydroxyethyl)-N-octadecylammonio]-butane-1-carboxylate;5-[S-3-hydroxypropyl-S-hexadecylsulfonio]-3-hydroxypentane-1-sulfate;3-[P,P-diethyl-P-3,6,9-trioxatetracosanephosphonio]-2-hydroxypropane-1-phosphate;3-[N,N-dipropyl-N-3-dodecoxy-2-hydroxypropyl-ammonio]-propane-1-phosphonate;3-(N,N-dimethyl-N-hexadecylammonio)-propane-1-sulfonate;3-(N,N-dimethyl-N-hexadecylammonio)-2-hydroxy-propane-1-sulfonate;4-[N,N-di(2(2-hydroxyethyl)-N(2-hydroxydodecyl)ammonio]-butane-1-carboxylate;3-[S-ethyl-S-(3-dodecoxy-2-hydroxypropyl)sulfonio]-propane-1-phosphate;3-[P,P-dimethyl-P-dodecylphosphonio]-propane-1-phosphonate; and S[N,N-di(3-hydroxypropyl)-N-hexadecylammonio]-2-hydroxy-pentane-1-sulfate.The alkyl groups contained in said detergent surfactants can be straightor branched and saturated or unsaturated.

The zwitterionic surfactant suitable for use in the present compositionsincludes a betaine of the general structure:

These surfactant betaines typically do not exhibit strong cationic oranionic characters at pH extremes nor do they show reduced watersolubility in their isoelectric range. Unlike “external” quaternaryammonium salts, betaines are compatible with anionics. Examples ofsuitable betaines include coconut acylamidopropyldimethyl betaine;hexadecyl dimethyl betaine; C₁₂₋₁₄ acylamidopropylbetaine; C₈₋₁₄acylamidohexyldiethyl betaine; 4-C₁₄₋₁₆acylmethylamidodiethylammonio-1-carboxybutane; C₁₆₋₁₈acylamidodimethylbetaine; C₁₂₋₁₆ acylamidopentanediethylbetaine; andC₁₂₋₁₆ acylmethylamidodimethylbetaine.

Sultaines useful in the present invention include those compounds havingthe formula (R(R¹)₂N⁺R²SO³⁻, in which R is a C₆-C₁₈ hydrocarbyl group,each R¹ is typically independ C₁-C₃ alkyl, e.g. methyl, and R² is aC₁-C₆ hydrocarbyl group, e.g. a C₁-C₃ alkylene or hydroxyalkylene group.

A typical listing of zwitterionic classes, and species of thesesurfactants, is given in U.S. Pat. No. 3,929,678 issued to Laughlin andHeuring on Dec. 30, 1975. Further examples are given in “Surface ActiveAgents and Detergents” (Vol. I and II by Schwartz, Perry and Berch).

In an embodiment, the compositions of the present invention include abetaine. For example, the compositions can include cocoamidopropylbetaine.

Other Additional Ingredients

In some embodiments, the compositions of the present invention caninclude other additional ingredients. Additional ingredients suitablefor use with the compositions of the present invention include, but arenot limited to, acidulants, stabilizing agents, e.g., chelating agentsor sequestrants, buffers, detergents, wetting agents, defoaming agents,thickeners, foaming agents, solidification agents, aesthetic enhancingagents (i.e., colorants, odorants, or perfumes)and other cleaningagents. These additional ingredients can be preformulated with thecompositions of the invention or added to the system before, after, orsubstantially simultaneously with the addition of the compositions ofthe present invention. Additionally, the compositions can be used inconjunction with one or more conventional cleaning agents, e.g., analkaline detergent.

Acidulants

In some embodiments, the compositions of the present invention includean acidulant. The acidulant can act as a catalyst for conversion ofcarboxylic acid to peroxycarboxylic acid. The acidulant can be effectiveto form a concentrate composition with pH of about 1 or less. Theacidulant can be effective to form a use composition with pH of about 5,about 5 or less, about 4, about 4 or less, about 3, about 3 or less,about 2, about 2 or less, or the like. In some embodiments, an acidulantcan be used to lower the pH of an alkaline cleaning solution to a pH ofabout 10, about 10 or less, about 9, about 9 or less, about 8, about 8or less, about 7, about 7 or less, about 6, or about 6 or less. In anembodiment, the acidulant includes an inorganic acid. Suitable inorganicacids include, but are not limited to, sulfuric acid, sodium bisulfate,phosphoric acid, nitric acid, hydrochloric acid. In some embodiments,the acidulant includes an organic acid. Suitable organic acids include,but are not limited to, methane sulfonic acid, ethane sulfonic acid,propane sulfonic acid, butane sulfonic acid, xylene sulfonic acid,benzene sulfonic acid, formic acid, acetic acid, mono, di, ortri-halocarboyxlic acids, picolinic acid, dipicolinic acid, and mixturesthereof. In some embodiments, the compositions of the present inventionare free or substantially free of a phosphorous based acid.

In some embodiments, acidulant selected can also function as astabilizing agent. Thus, the compositions of the present invention canbe substantially free of an additional stabilizing agent.

In certain embodiments, the present composition includes about 0.5 toabout 80 wt-% acidulant, about 1 to about 50 wt %, about 5 to about 30wt-% acidulant, or about 7 to about 14 wt-% acidulant. It is to beunderstood that all values and ranges between these values and rangesare encompassed by the compositions of the present invention.

Stabilizing Agents

In some embodiments, the compositions of the present invention includeone or more stabilizing agents. The stabilizing agents can be used, forexample, to stabilize the peracid and hydrogen peroxide and prevent thepremature oxidation of this constituent within the composition of theinvention.

In some embodiments, an acidic stabilizing agent can be used. Thus, insome embodiments, the compositions of the present invention can besubstantially free of an additional acidulant.

Suitable stabilizing agents include, for example, chelating agents orsequestrants. Suitable sequestrants include, but are not limited to,organic chelating compounds that sequester metal ions in solution,particularly transition metal ions. Such sequestrants include organicamino- or hydroxy-polyphosphonic acid complexing agents (either in acidor soluble salt forms), carboxylic acids (e.g., polymericpolycarboxylate), hydroxycarboxylic acids, aminocarboxylic acids, orheterocyclic carboxylic acids, e.g., pyridine-2,6-dicarboxylic acid(dipicolinic acid).

In some embodiments, the compositions of the present invention includedipicolinic acid as a stabilizing agent. Compositions includingdipicolinic acid can be formulated to be free or substantially free ofphosphorous. It has also been observed that the inclusion of dipicolinicacid in a composition of the present invention aids in achieving thephase stability of the compositions, compared to other conventionalstabilizing agents, e. 1-hydroxy ethylidene-1,1-diphosphonic acid(CH₃C(PO₃H₂)₂OH) (HEDP).

In other embodiments, the sequestrant can be or include phosphonic acidor phosphonate salt. Suitable phosphonic acids and phosphonate saltsinclude HEDP; ethylenediamine tetrakis methylenephosphonic acid (EDTMP);diethylenetriamine pentakis methylenephosphonic acid (DTPMP);cyclohexane-1,2-tetramethylene phosphonic acid; amino[tri(methylenephosphonic acid)]; (ethylene diamine[tetra methylene-phosphonic acid)];2-phosphene butane-1,2,4-tricarboxylic acid; or salts thereof, such asthe alkali metal salts, ammonium salts, or alkyloyl amine salts, such asmono, di, or tetra-ethanolamine salts; picolinic, dipicolinic acid ormixtures thereof. In some embodiments, organic phosphonates, e.g, HEDPare included in the compositions of the present invention.

Commercially available food additive chelating agents includephosphonates sold under the trade name DEQUEST® including, for example,1-hydroxyethylidene-1,1-diphosphonic acid, available from MonsantoIndustrial Chemicals Co., St. Louis, Mo., as DEQUEST® 2010;amino(tri(methylenephosphonic acid)), (N[CH₂PO₃H₂]₃), available fromMonsanto as DEQUEST® 2000; ethylenediamine[tetra(methylenephosphonicacid)] available from Monsanto as DEQUEST® 2041; and2-phosphonobutane-1,2,4-tricarboxylic acid available from Mobay ChemicalCorporation, Inorganic Chemicals Division, Pittsburgh, Pa., as BayhibitAM.

The sequestrant can be or include aminocarboxylic acid type sequestrant.Suitable aminocarboxylic acid type sequestrants include the acids oralkali metal salts thereof, e.g., amino acetates and salts thereofSuitable aminocarboxylates include N-hydroxyethylaminodiacetic acid;hydroxyethylenediaminetetraacetic acid, nitrilotriacetic acid (NTA);ethylenediaminetetraacetic acid (EDTA);N-hydroxyethyl-ethylenediaminetriacetic acid (HEDTA);diethylenetriaminepentaacetic acid (DTPA); and alanine-N,N-diaceticacid; and the like; and mixtures thereof.

The sequestrant can be or include a polycarboxylate. Suitablepolycarboxylates include, for example, polyacrylic acid, maleic/olefincopolymer, acrylic/maleic copolymer, polymethacrylic acid, acrylicacid-methacrylic acid copolymers, hydrolyzed polyacrylamide, hydrolyzedpolymethacrylamide, hydrolyzed polyamide-methacrylamide copolymers,hydrolyzed polyacrylonitrile, hydrolyzed polymethacrylonitrile,hydrolyzed acrylonitrile-methacrylonitrile copolymers, polymaleic acid,polyfumaric acid, copolymers of acrylic and itaconic acid, phosphinopolycarboxylate, acid or salt forms thereof, mixtures thereof, and thelike.

In certain embodiments, the present composition includes about 0.01 toabout 10 wt-% stabilizing agent, about 0.4 to about 4 wt-% stabilizingagent, about 0.6 to about 3 wt-% stabilizing agent, about 1 to about 2wt-% stabilizing agent. It is to be understood that all values andranges within these values and ranges are encompassed by the presentinvention.

Wetting or Defoaming Agents

Also useful in the compositions of the invention are wetting anddefoaming agents. Wetting agents function to increase the surfacecontact or penetration activity of the antimicrobial composition of theinvention. Wetting agents which can be used in the composition of theinvention include any of those constituents known within the art toraise the surface activity of the composition of the invention.

Generally, defoamers which can be used in accordance with the inventioninclude silica and silicones; aliphatic acids or esters; alcohols;sulfates or sulfonates; amines or amides; halogenated compounds such asfluorochlorohydrocarbons; vegetable oils, waxes, mineral oils as well astheir sulfonated or sulfated derivatives; fatty acids and/or their soapssuch as alkali, alkaline earth metal soaps; and phosphates and phosphateesters such as alkyl and alkaline diphosphates, and tributyl phosphatesamong others; and mixtures thereof.

In some embodiments, the compositions of the present invention caninclude antifoaming agents or defoamers which are of food grade qualitygiven the application of the method of the invention. To this end, oneof the more effective antifoaming agents includes silicones. Siliconessuch as dimethyl silicone, glycol polysiloxane, methylphenolpolysiloxane, trialkyl or tetralkyl silanes, hydrophobic silicadefoamers and mixtures thereof can all be used in defoamingapplications. Commercial defoamers commonly available include siliconessuch as Ardefoam® from Armour Industrial Chemical Company which is asilicone bound in an organic emulsion; Foam Kill® or Kresseo® availablefrom Kirusable Chemical Company which are silicone and non-silicone typedefoamers as well as silicone esters; and Anti-Foam A® and DC-200 fromDow Corning Corporation which are both food grade type silicones amongothers. These defoamers can be present at a concentration range fromabout 0.01 wt-% to 20 wt-%, from about 0.01 wt-% to 5 wt-%, or fromabout 0.01 wt-% to about 1 wt-%.

Thickening or Gelling Agents

The compositions of the present invention can include any of a varietyof known thickeners. Suitable thickeners include natural gums such asxanthan gum, guar gum, or other gums from plant mucilage; polysaccharidebased thickeners, such as alginates, starches, and cellulosic polymers(e.g., carboxymethyl cellulose); polyacrylates thickeners; andhydrocolloid thickeners, such as pectin. In an embodiment, the thickenerdoes not leave contaminating residue on the surface of an object. Forexample, the thickeners or gelling agents can be compatible with food orother sensitive products in contact areas. Generally, the concentrationof thickener employed in the present compositions or methods will bedictated by the desired viscosity within the final composition. However,as a general guideline, the viscosity of thickener within the presentcomposition ranges from about 0.1 wt-% to about 5 wt-%, from about 0.1wt-% to about 1.0 wt-%, or from about 0.1 wt-% to about 0.5 wt-%.

Solidification Agent

The present compositions can include a solidification agent, which canparticipate in maintaining the compositions in a solid form. In someembodiments, the solidification agent can form and/or maintain thecomposition as a solid. In other embodiments, the solidification agentcan solidify the composition without unacceptably detracting from theeventual release of the sulfonated peroxycarboxylic acid. Thesolidification agent can include, for example, an organic or inorganicsolid compound having a neutral inert character or making a functional,stabilizing or detersive contribution to the present composition.Suitable solidification agents include solid polyethylene glycol (PEG),solid polypropylene glycol, solid EO/PO block copolymer, amide, urea(also known as carbamide), nonionic surfactant (which can be employedwith a coupler), anionic surfactant, starch that has been madewater-soluble (e.g., through an acid or alkaline treatment process),cellulose that has been made water-soluble, inorganic agent, poly(maleicanhydride/methyl vinyl ether), polymethacrylic acid, other generallyfunctional or inert materials with high melting points, mixturesthereof, and the like;

Suitable glycol solidification agents include a solid polyethyleneglycol or a solid polypropylene glycol, which can, for example, havemolecular weight of about 1,400 to about 30,000. In certain embodiments,the solidification agent includes or is solid PEG, for example PEG 1500up to PEG 20,000. In certain embodiments, the PEG includes PEG 1450, PEG3350, PEG 4500, PEG 8000, PEG 20,000, and the like. Suitable solidpolyethylene glycols are commercially available from Union Carbide underthe tradename CARBOWAX.

Suitable amide solidification agents include stearic monoethanolamide,lauric diethanolamide, stearic diethanolamide, stearic monoethanolamide, cocodiethylene amide, an alkylamide, mixtures thereof, and thelike. In an embodiment, the present composition can include glycol(e.g., PEG) and amide.

Suitable nonionic surfactant solidification agents include nonylphenolethoxylate, linear alkyl alcohol ethoxylate, ethylene oxide/propyleneoxide block copolymer, mixtures thereof, or the like. Suitable ethyleneoxide/propylene oxide block copolymers include those sold under thePluronic tradename (e.g., Pluronic 108 and Pluronic F68) andcommercially available from BASF Corporation. In some embodiments, thenonionic surfactant can be selected to be solid at room temperature orthe temperature at which the composition will be stored or used. Inother embodiments, the nonionic surfactant can be selected to havereduced aqueous solubility in combination with the coupling agent.Suitable couplers that can be employed with the nonionic surfactantsolidification agent include propylene glycol, polyethylene glycol,mixtures thereof, or the like.

Suitable anionic surfactant solidification agents include linear alkylbenzene sulfonate, alcohol sulfate, alcohol ether sulfate, alpha olefinsulfonate, mixtures thereof, and the like. In an embodiment, the anionicsurfactant solidification agent is or includes linear alkyl benzenesulfonate. In an embodiment, the anionic surfactant can be selected tobe solid at room temperature or the temperature at which the compositionwill be stored or used.

Suitable inorganic solidification agents include phosphate salt (e.g.,alkali metal phosphate), sulfate salt (e.g., magnesium sulfate, sodiumsulfate or sodium bisulfate), acetate salt (e.g., anhydrous sodiumacetate), Borates (e.g., sodium borate), Silicates (e.g., theprecipitated or fumed forms (e.g., Sipernat 50® available from Degussa),carbonate salt (e.g., calcium carbonate or carbonate hydrate), otherknown hydratable compounds, mixtures thereof, and the like. In anembodiment, the inorganic solidification agent can include organicphosphonate compound and carbonate salt, such as an E-Form composition.

In some embodiments, the compositions of the present invention caninclude any agent or combination of agents that provide a requisitedegree of solidification and aqueous solubility can be included in thepresent compositions. In other embodiments, increasing the concentrationof the solidification agent in the present composition can tend toincrease the hardness of the composition. In yet other embodiments,decreasing the concentration of solidification agent can tend to loosenor soften the concentrate composition.

In some embodiments, the solidification agent can include any organic orinorganic compound that imparts a solid character to and/or controls thesoluble character of the present composition, for example, when placedin an aqueous environment. For example, a solidifying agent can providecontrolled dispensing if it has greater aqueous solubility compared toother ingredients in the composition. Urea can be one suchsolidification agent. By way of further example, for systems that canbenefit from less aqueous solubility or a slower rate of dissolution, anorganic nonionic or amide hardening agent may be appropriate.

In some embodiments, the compositions of the present invention caninclude a solidification agent that provides for convenient processingor manufacture of the present composition. For example, thesolidification agent can be selected to form a composition that canharden to a solid form under ambient temperatures of about 30 to about50° C. after mixing ceases and the mixture is dispensed from the mixingsystem, within about 1 minute to about 3 hours, or about 2 minutes toabout 2 hours, or about 5 minutes to about 1 hour.

The compositions of the present invention can include solidificationagent at any effective amount. The amount of solidification agentincluded in the present composition can vary according to the type ofcomposition, the ingredients of the composition, the intended use of thecomposition, the quantity of dispensing solution applied to the solidcomposition over time during use, the temperature of the dispensingsolution, the hardness of the dispensing solution, the physical size ofthe solid composition, the concentration of the other ingredients, theconcentration of the cleaning agent in the composition, and other likefactors. Suitable amounts can include about 1 to about 99 wt-%, about1.5 to about 85 wt-%, about 2 to about 80 wt-%, about 10 to about 45wt-%, about 15% to about 40 wt-%, about 20% to about 30 wt-%, about 30%to about 70%, about 40% to about 60%, up to about 50 wt-%, about 40% toabout 50%

Carrier

In some embodiments, the compositions of the present invention include acarrier. The carrier provides a medium which dissolves, suspends, orcarries the other components of the composition. For example, thecarrier can provide a medium for solubilization, suspension, orproduction of a sulfonated peroxycarboxylic acid and for forming anequilibrium mixture. The carrier can also function to deliver and wetthe composition of the invention on an object. To this end, the carriercan contain any component or components that can facilitate thesefunctions.

In some embodiments, the carrier includes primarily water which canpromote solubility and work as a medium for reaction and equilibrium.The carrier can include or be primarily an organic solvent, such assimple alkyl alcohols, e.g., ethanol, isopropanol, n-propanol, benzylalcohol, and the like. Polyols are also useful carriers, includingglycerol, sorbitol, and the like.

Suitable carriers include glycol ethers. Suitable glycol ethers includediethylene glycol n-butyl ether, diethylene glycol n-propyl ether,diethylene glycol ethyl ether, diethylene glycol methyl ether,diethylene glycol t-butyl ether, dipropylene glycol n-butyl ether,dipropylene glycol methyl ether, dipropylene glycol ethyl ether,dipropylene glycol propyl ether, dipropylene glycol tert-butyl ether,ethylene glycol butyl ether, ethylene glycol propyl ether, ethyleneglycol ethyl ether, ethylene glycol methyl ether, ethylene glycol methylether acetate, propylene glycol n-butyl ether, propylene glycol ethylether, propylene glycol methyl ether, propylene glycol n-propyl ether,tripropylene glycol methyl ether and tripropylene glycol n-butyl ether,ethylene glycol phenyl ether (commercially available as DOWANOL EPH™from Dow Chemical Co.), propylene glycol phenyl ether (commerciallyavailable as DOWANOL PPH™ from Dow Chemical Co.), and the like, ormixtures thereof Additional suitable commercially available glycolethers (all of which are available from Union Carbide Corp.) includeButoxyethyl PROPASOL™, Butyl CARBITOL™ acetate, Butyl CARBITOL™, ButylCELLOSOLVE™ acetate, Butyl CELLOSOLVE™, Butyl DIPROPASOL™, ButylPROPASOL™, CARBITOL™ PM-600, CARBITOL™ Low Gravity, CELLOSOLVE™ acetate,CELLOSOLVE™, Ester EEP™, FILMER IBT™, Hexyl CARBITOL™, HexylCELLOSOLVE™, Methyl CARBITOL™, Methyl CELLOSOLVE™ acetate, MethylCELLOSOLVE™, Methyl DIPROPASOL™, Methyl PROPASOL™ acetate, MethylPROPASOL™, Propyl CARBITOL™, Propyl CELLOSOLVE™, Propyl DIPROPASOL™ andPropyl PROPASOL™.

In some embodiments, the carrier makes up a large portion of thecomposition of the invention and may be the balance of the compositionapart from the sulfonated peroxycarboxylic acid, oxidizing agent,additional ingredients, and the like. The carrier concentration and typewill depend upon the nature of the composition as a whole, theenvironmental storage, and method of application including concentrationof the sulfonated peroxycarboxylic acid, among other factors. Notablythe carrier should be chosen and used at a concentration which does notinhibit the efficacy of the sulfonated peroxycarboxylic acid in thecomposition of the invention for the intended use, e.g., bleaching,sanitizing, disinfecting.

In certain embodiments, the present composition includes about 5 toabout 90 wt-% carrier, about 10 to about 80 wt % carrier, about 20 toabout 60 wt % carrier, or about 30 to about 40 wt % carrier. It is to beunderstood that all values and ranges between these values and rangesare encompassed by the present invention.

Use Compositions

The compositions of the present invention include concentratecompositions and use compositions. For example, a concentratecomposition can be diluted, for example with water, to form a usecomposition. In an embodiment, a concentrate composition can be dilutedto a use solution before to application to an object. For reasons ofeconomics, the concentrate can be marketed and an end user can dilutethe concentrate with water or an aqueous diluent to a use solution.

The level of active components in the concentrate composition isdependent on the intended dilution factor and the desired activity ofthe sulfonated peroxycarboxylic acid compound. Generally, a dilution ofabout 1 fluid ounce to about 10 gallons of water to about 10 fluidounces to about 1 gallon of water is used for aqueous compositions ofthe present invention. In some embodiments, higher use dilutions can beemployed if elevated use temperature (greater than 25° C.) or extendedexposure time (greater than 30 seconds) can be employed. In the typicaluse locus, the concentrate is diluted with a major proportion of waterusing commonly available tap or service water mixing the materials at adilution ratio of about 3 to about 40 ounces of concentrate per 100gallons of water.

In some embodiments, when used in a laundry application, theconcentrated compositions can be diluted at a dilution ratio of about0.1 g/L to about 100 g/L concentrate to diluent, about 0.5 g/L to about10.0 g/L concentrate to diluent, about 1.0 g/L to about 4.0 g/Lconcentrate to diluent, or about 1.0 g/L to about 2.0 g/L concentrate todiluent.

In other embodiments, a use composition can include about 0.01 to about10 wt-% of a concentrate composition and about 90 to about 99.99 wt-%diluent; or about 0.1 to about 1 wt-% of a concentrate composition andabout 99 to about 99.9 wt-% diluent.

Amounts of an ingredient in a use composition can be calculated from theamounts listed above for concentrate compositions and these dilutionfactors. In some embodiments, for example when used in a laundryapplication, the concentrated compositions of the present invention arediluted such that the sulfopercarboxylic acid is present at from about20 ppm to about 80 ppm. In other embodiments, the concentratedcompositions of the present invention are diluted such that thesulfopercarboxylic acid is present at about 20 ppm, about 40 ppm, about60 ppm, about 80 ppm, about 500 ppm, about 1000 ppm, or about 10,000 toabout 20,000 ppm. It is to be understood that all values and rangesbetween these values and ranges are encompassed by the presentinvention.

Methods Employing the Sulfoperoxycarboxylic Acid Compounds andCompositions

In some aspects, the present invention includes methods of using thesulfoperoxycarboxylic acid compounds and compositions of the presentinvention. In some embodiments, these methods employ the antimicrobialand/or bleaching activity of the sulfoperoxycarboxylic acid. Forexample, the invention includes a method for reducing a microbialpopulation, a method for reducing the population of a microorganism onskin, a method for treating a disease of skin, a method for reducing anodor, and/or a method for bleaching. These methods can operate on anarticle, surface, in a body or stream of water or a gas, or the like, bycontacting the article, surface, body, or stream with asulfoperoxycarboxylic acid compound or composition of the invention.Contacting can include any of numerous methods for applying a compoundor composition of the invention, such as spraying the compounds orcompositions, immersing the article in the compounds or compositions,foam or gel treating the article with the compounds or composition, or acombination thereof.

In some aspects, a composition of the present invention includes anamount of sulfoperoxycarboxylic acid of the present invention effectivefor killing one or more of the food-borne pathogenic bacteria associatedwith a food product, including, but not limited to, Salmonellatyphimurium, Salmonella javiana, Campylobacter jejuni, Listeriamonocytogenes, and Escherichia coli O157:H7, yeast, and mold. In someembodiments, the compositions of the present invention include an amountof sulfoperoxycarboxylic acid effective for killing one or more of thepathogenic bacteria associated with a health care surfaces andenvironments including, but not limited to, Salmonella typhimurium,Staphylococcus aureus, methicilin resistant Staphylococcus aureus,Salmonella choleraesurus, Pseudomonas aeruginosa, Escherichia coli,mycobacteria, yeast, and mold. The compounds and compositions of thepresent invention have activity against a wide variety of microorganismssuch as Gram positive (for example, Listeria monocytogenes orStaphylococcus aureus) and Gram negative (for example, Escherichia colior Pseudomonas aeruginosa) bacteria, yeast, molds, bacterial spores,viruses, etc. The compounds and compositions of the present invention,as described above, have activity against a wide variety of humanpathogens. The present compounds and compositions can kill a widevariety of microorganisms on a food processing surface, on the surfaceof a food product, in water used for washing or processing of foodproduct, on a health care surface, or in a health care environment.

The compounds of the invention can be used for a variety of domestic orindustrial applications, e.g., to reduce microbial or viral populationson a surface or object or in a body or stream of water. The compoundscan be applied in a variety of areas including kitchens, bathrooms,factories, hospitals, dental offices and food plants, and can be appliedto a variety of hard or soft surfaces having smooth, irregular or poroustopography. Suitable hard surfaces include, for example, architecturalsurfaces (e.g., floors, walls, windows, sinks, tables, counters andsigns); eating utensils; hard-surface medical or surgical instrumentsand devices; and hard-surface packaging. Such hard surfaces can be madefrom a variety of materials including, for example, ceramic, metal,glass, wood or hard plastic. Suitable soft surfaces include, for examplepaper; filter media; hospital and surgical linens and garments;soft-surface medical or surgical instruments and devices; andsoft-surface packaging. Such soft surfaces can be made from a variety ofmaterials including, for example, paper, fiber, woven or nonwovenfabric, soft plastics and elastomers. The compounds of the invention canalso be applied to soft surfaces such as food and skin (e.g., a hand).The present compounds can be employed as a foaming or nonfoamingenvironmental sanitizer or disinfectant.

The compounds and compositions of the invention can be included inproducts such as sterilants, sanitizers, disinfectants, preservatives,deodorizers, antiseptics, fungicides, germicides, sporicides, virucides,detergents, bleaches, hard surface cleaners, hand soaps, waterless handsanitizers, and pre- or post-surgical scrubs.

The compounds can also be used in veterinary products such as mammalianskin treatments or in products for sanitizing or disinfecting animalenclosures, pens, watering stations, and veterinary treatment areas suchas inspection tables and operation rooms. The present compounds can beemployed in an antimicrobial foot bath for livestock or people. Thecompounds of the present invention can also be employed as anantimicrobial teat dip.

In some aspects, the compounds of the present invention can be employedfor reducing the population of pathogenic microorganisms, such aspathogens of humans, animals, and the like. The compounds exhibitactivity against pathogens including fungi, molds, bacteria, spores, andviruses, for example, S. aureus, E. coli, Streptococci, Legionella,Pseudomonas aeruginosa, mycobacteria, tuberculosis, phages, or the like.Such pathogens can cause a variety of diseases and disorders, includingmastitis or other mammalian milking diseases, tuberculosis, and thelike. The compounds of the present invention can reduce the populationof microorganisms on skin or other external or mucosal surfaces of ananimal. In addition, the present compounds can kill pathogenicmicroorganisms that spread through transfer by water, air, or a surfacesubstrate. The compounds need only be applied to the skin, otherexternal or mucosal surfaces of an animal water, air, or surface.

In some embodiments, the compounds and compositions of the presentinvention can be used to reduce the population of prions on a surface.Prions are proteinaceous infections particles free of nucleic acid.Prions are known to cause several brain diseases including kuru,Creutzfeldt-Jakob disease, Gerstmann-Straussler-Scheinker disease, andfatal familial insomnia in humans; scrapie in sheep; bovine spongiformencephalopathy (Mad Cow Disease) in cattle; transmissible minkencephalopathy in mink; chronic wasting disease in deer and elk; andfeline spongiform encephalopathy in cats. These diseases lead tosymptoms including dementia, ataxia, behavioral disturbances, dizziness,involuntary movement, and death. Prions can be transmitted by exposureto infected tissue and brain tissue, spinal cord tissue, pituitarytissue, and eye tissue in particular. In some embodiments, the compoundsand compositions of the present invention can be used to reduce apopulation of prions according to a method as described in U.S. Pat. No.7,470,655, the entire contents of which are hereby incorporated byreference.

The antimicrobial compounds can also be used on foods and plant speciesto reduce surface microbial populations; used at manufacturing orprocessing sites handling such foods and plant species; or used to treatprocess waters around such sites. For example, the compounds can be usedon food transport lines (e.g., as belt sprays); boot and hand-washdip-pans; food storage facilities; anti-spoilage air circulationsystems; refrigeration and cooler equipment; beverage chillers andwarmers, blanchers, cutting boards, third sink areas, and meat chillersor scalding devices. The compounds of the invention can be used to treatproduce transport waters such as those found in flumes, pipe transports,cutters, slicers, blanchers, retort systems, washers, and the like.Particular foodstuffs that can be treated with compounds of theinvention include eggs, meats, seeds, leaves, fruits and vegetables.Particular plant surfaces include both harvested and growing leaves,roots, seeds, skins or shells, stems, stalks, tubers, corms, fruit, andthe like. The compounds may also be used to treat animal carcasses toreduce both pathogenic and non-pathogenic microbial levels.

The antimicrobial compounds can also be used to treat waste water whereboth its antimicrobial function and its oxidant properties can beutilized. Aside from the microbial issues surrounding waste water, it isoften rich in malodorous compounds of reduced sulfur, nitrogen orphosphorous. A strong oxidant such as the present invention convertsthese compounds efficiently to their odor free derivatives e.g. thesulfates, phosphates and amine oxides. These same properties are veryuseful in the pulp and paper industry where the property of bleaching isalso of great utility.

In some aspects, the compounds of the present invention can be employedfor epoxidations. The polymer industry is a major consumer of peracids,especially peroxyacetic acid but the typical equilibrium peroxyaceticacid also includes some strong acid residues which are problematic forthe epoxide derivatives. A stable peracid isolate is thereforepotentially of great utility in this industry.

In some aspects, the compounds and compositions of the present inventionare useful in the cleaning or sanitizing of containers, processingfacilities, or equipment in the food service or food processingindustries. The compounds and compositions have particular value for useon food packaging materials and equipment, and especially for cold orhot aseptic packaging. Examples of process facilities in which thecompound of the invention can be employed include a milk line dairy, acontinuous brewing system, food processing lines such as pumpable foodsystems and beverage lines, etc. Food service wares can be disinfectedwith the compound of the invention. For example, the compounds can alsobe used on or in ware wash machines, low temperature ware wash machines,dishware, bottle washers, bottle chillers, warmers, third sink washers,cutting areas (e.g., water knives, slicers, cutters and saws) and eggwashers. Particular treatable surfaces include packaging such ascartons, bottles, films and resins; dish ware such as glasses, plates,utensils, pots and pans; ware wash and low temperature ware washmachines; exposed food preparation area surfaces such as sinks,counters, tables, floors and walls; processing equipment such as tanks,vats, lines, pumps and hoses (e.g., dairy processing equipment forprocessing milk, cheese, ice cream and other dairy products); andtransportation vehicles. Containers include glass bottles, PVC orpolyolefin film sacks, cans, polyester, PEN or PET bottles of variousvolumes (100 ml to 2 liter, etc.), one gallon milk containers, paperboard juice or milk containers, etc.

The compounds and compositions can also be used on or in otherindustrial equipment and in other industrial process streams such asheaters, cooling towers, boilers, retort waters, rinse waters, asepticpackaging wash waters, and the like. The compounds can be used to treatmicrobes and odors in recreational waters such as in pools, spas,recreational flumes and water slides, fountains, and the like.

A filter containing the compound can reduce the population ofmicroorganisms in air and liquids. Such a filter can remove water andair-born pathogens such as Legionella.

The present compounds can be employed for reducing the population ofmicrobes, fruit flies, or other insect larva on a drain or othersurface.

The compounds of the present invention can also be employed by dippingfood processing equipment into the use solution, soaking the equipmentfor a time sufficient to sanitize the equipment, and wiping or drainingexcess solution off the equipment, The compound may be further employedby spraying or wiping food processing surfaces with the use solution,keeping the surfaces wet for a time sufficient to sanitize the surfaces,and removing excess solution by wiping, draining vertically, vacuuming,etc.

The compounds of the present invention may also be used in a method ofsanitizing hard surfaces such as institutional type equipment, utensils,dishes, health care equipment or tools, and other hard surfaces.

The antimicrobial compounds can be applied to microbes or to soiled orcleaned surfaces using a variety of methods. These methods can operateon an object, surface, in a body or stream of water or a gas, or thelike, by contacting the object, surface, body, or stream with a compoundof the invention. Contacting can include any of numerous methods forapplying a compound, such as spraying the compound, immersing the objectin the compound, foam or gel treating the object with the compound, or acombination thereof.

A concentrate or use concentration of a compound of the presentinvention can be applied to or brought into contact with an object byany conventional method or apparatus for applying an antimicrobial orcleaning compound to an object. For example, the object can be wipedwith, sprayed with, foamed on, and/or immersed in the compound, or a usesolution made from the compound. The compound can be sprayed, foamed, orwiped onto a surface; the compound can be caused to flow over thesurface, or the surface can be dipped into the compound. Contacting canbe manual or by machine. Food processing surfaces, food products, foodprocessing or transport waters, and the like can be treated with liquid,foam, gel, aerosol, gas, wax, solid, or powdered stabilized compoundsaccording to the invention, or solutions containing these compounds.

Laundry Applications

In some aspects, the compounds and compositions can also be employed insanitizing articles, e.g., textiles, which have become contaminated. Thearticles are contacted with the compounds of the invention at usetemperatures in the range of about 4° C. to 80° C., for a period of timeeffective to sanitize, disinfect, and/or sterilize the articles. In someembodiments, the compounds of the present invention can be used tobleach and/or sanitize articles at a temperature of about 30° C. toabout 50° C. or about 40° C. For example, in some embodiments, thecompounds of the present invention can be injected into the wash orrinse water of a laundry machine and contacted with contaminated fabricfor a time sufficient to sanitize the fabric. In some embodiments, thecontaminated fabric is contacted with the compounds and compositions ofthe present invention for about 5 to about 30 minutes. Excess solutioncan then be removed by rinsing or centrifuging the fabric.

In some aspects, the compounds and compositions of the present inventioncan be used as a bleaching agent to whiten or lighten or remove stainsfrom a substrate, e.g., hard surface, or fabric. The compounds of thepresent invention can be used to bleach or remove stains from anyconventional textile, including but not limited to, cotton, poly-cottonblends, wool, and polyesters. The compounds of the present invention arealso textile tolerant, i.e., they will not substantially degrade thetextile to which they are applied. The compounds of the presentinvention can be used to remove a variety of stains from a variety ofsources including, but not limited to, lipstick, pigment/sebum,pigment/lanolin, soot, olive oil, mineral oil, motor oil, blood,make-up, red wine, tea, ketchup, and combinations thereof.

In some embodiments, the compounds of the present invention can be usedas a low odor, acidic bleaching agent. In some embodiments, thecompounds of the present invention can be used as a low odor bleachingagent at a neutral pH, i.e., about 7. In some embodiments, the compoundsof the present invention can be used at an alkaline pH, e.g., about 8,9, or 10. In still yet other embodiments, the compounds of the presentinvention can be used as an all in one sour, bleaching and sterilantproduct.

The compounds and compositions of the present invention can be usedalone to treat the articles, e.g., textiles, or can be used inconjunction with conventional detergents suitable for the articles to betreated. The compounds and compositions of the invention can be usedwith conventional detergents in a variety of ways, for example, thecompounds and compositions of the invention can be formulated with aconventional detergent. In other embodiments, the compounds andcompositions of the invention can be used to treat the article as aseparate additive from a conventional detergent. When used as a separateadditive, the compounds and compositions of the present invention cancontact the article to be treated at any time. For example, thecompounds and compositions of the invention can contact the articlebefore, after, or substantially simultaneously as the articles arecontacted with the selected detergent.

In some embodiments, when used as a bleaching and/orsanitizing/disinfecting agent for a laundry application, a compound ormixture of compounds of the present invention will be present in acomposition at about 5 ppm to about 1000 ppm. In other embodiments, whenused as a bleaching and/or sanitizing/disinfecting agent for a laundryapplication, a compound or mixture of compounds of the present inventionwill be present in a composition at about 25 ppm to about 100 ppm. Inother embodiments, when used as a bleaching and/orsanitizing/disinfecting agent in a laundry application, a compound ormixture thereof of the present invention will be present at about 20,about 40, about 60, or about 80 ppm. In still yet other embodiments, acompound or mixture of compounds of the present invention itself will beused as a bleaching agent, i.e., the compound or mixture of compoundswill be present in a composition at about 100 wt %.

Clean in Place

Other hard surface cleaning applications for the compounds of thepresent invention include clean-in-place systems (CIP),clean-out-of-place systems (COP), washer-decontaminators, sterilizers,textile laundry machines, ultra and nano-filtration systems and indoorair filters. COP systems can include readily accessible systemsincluding wash tanks, soaking vessels, mop buckets, holding tanks, scrubsinks, vehicle parts washers, non-continuous batch washers and systems,and the like. CIP systems include the internal components of tanks,lines, pumps and other process equipment used for processing typicallyliquid product streams such as beverages, milk, juices.

Generally, the actual cleaning of the in-place system or other surface(i.e., removal of unwanted offal therein) is accomplished with adifferent material such as a formulated detergent which is introducedwith heated water. After this cleaning step, the instant compositionwould be applied or introduced into the system at a use solutionconcentration in unheated, ambient temperature water. CIP typicallyemploy flow rates on the order of about 40 to about 600 liters perminute, temperatures from ambient up to about 70° C., and contact timesof at least about 10 seconds, for example, about 30 to about 120seconds. The present composition can remain in solution in cold (e.g.,40° F./4° C.) water and heated (e.g., 140° F./60° C.) water. Although itis not normally necessary to heat the aqueous use solution of thepresent composition, under some circumstances heating may be desirableto further enhance its activity. These materials are useful at anyconceivable temperatures.

A method of sanitizing substantially fixed in-place process facilitiesincludes the following steps. The use solution of the invention isintroduced into the process facilities at a temperature in the range ofabout 4° C. to 60° C. After introduction of the use solution, thesolution is held in a container or circulated throughout the system fora time sufficient to sanitize the process facilities (e.g., to killundesirable microorganisms). After the surfaces have been sanitized bymeans of the present composition, the use solution is drained. Uponcompletion of the sanitizing step, the system optionally may be rinsedwith other materials such as potable water. The composition can becirculated through the process facilities for 10 minutes or less.

The present method can include delivering the present composition viaair delivery to the clean-in-place or other surfaces such as thoseinside pipes and tanks. This method of air delivery can reduce thevolume of solution required.

Methods for Contacting a Food Product

In some aspects, the present invention provides methods for contacting afood product with a sulfoperoxycarboxylic acid compounds or compositionemploying any method or apparatus suitable for applying such a compoundor composition. For example, in some embodiments, the food product iscontacted by a compound of the present invention with a spray of thecompound, by immersion in the compound, by foam or gel treating with thecompound. Contact with a spray, a foam, a gel, or by immersion can beaccomplished by a variety of methods known to those of skill in the artfor applying antimicrobial agents to food. Contacting the food productcan occur in any location in which the food product might be found, suchas field, processing site or plant, vehicle, warehouse, store,restaurant, or home. These same methods can also be adapted to apply thecompounds of the present invention to other objects.

The present methods require a certain minimal contact time of thecompound with food product for occurrence of significant antimicrobialeffect. The contact time can vary with concentration of the usecompound, method of applying the use compound, temperature of the usecompound, amount of soil on the food product, number of microorganismson the food product, type of antimicrobial agent, or the like. Theexposure time can be at least about 5 to about 15 seconds. In someembodiments, the exposure time is about 15 to about 30 seconds. In otherembodiments, the exposure time is at least about 30 seconds.

In some embodiments, the method for washing a food product employs apressure spray including a compound of the present invention. Duringapplication of the spray solution on the food product, the surface ofthe food product can be moved with mechanical action, e.g., agitated,rubbed, brushed, etc. Agitation can be by physical scrubbing of the foodproduct, through the action of the spray solution under pressure,through sonication, or by other methods. Agitation increases theefficacy of the spray solution in killing micro-organisms, perhaps dueto better exposure of the solution into the crevasses or small coloniescontaining the micro-organisms. The spray solution, before application,can also be heated to a temperature of about 15 to 20° C., for example,about 20 to 60° C. to increase efficacy. The spray stabilized compoundcan be left on the food product for a sufficient amount of time tosuitably reduce the population of microorganisms, and then rinsed,drained, or evaporated off the food product.

Application of the material by spray can be accomplished using a manualspray wand application, an automatic spray of food product moving alonga production line using multiple spray heads to ensure complete contact,or other spray apparatus. One automatic spray application involves theuse of a spray booth. The spray booth substantially confines the sprayedcompound to within the booth. The production line moves the food productthrough the entryway into the spray booth in which the food product issprayed on all its exterior surfaces with sprays within the booth. Aftera complete coverage of the material and drainage of the material fromthe food product within the booth, the food product can then exit thebooth. The spray booth can include steam jets that can be used to applythe stabilized compounds of the invention. These steam jets can be usedin combination with cooling water to ensure that the treatment reachingthe food product surface is less than 65° C., e.g., less than 60° C. Thetemperature of the spray on the food product is important to ensure thatthe food product is not substantially altered (cooked) by thetemperature of the spray. The spray pattern can be virtually any usefulspray pattern.

Immersing a food product in a liquid stabilized compound of the presentinvention can be accomplished by any of a variety of methods known tothose of skill in the art. For example, the food product can be placedinto a tank or bath containing the stabilized compound. Alternatively,the food product can be transported or processed in a flume of thestabilized compound. The washing solution can be agitated to increasethe efficacy of the solution and the speed at which the solution reducesmicro-organisms accompanying the food product. Agitation can be obtainedby conventional methods, including ultrasonics, aeration by bubbling airthrough the solution, by mechanical methods, such as strainers, paddles,brushes, pump driven liquid jets, or by combinations of these methods.The washing solution can be heated to increase the efficacy of thesolution in killing micro-organisms. After the food product has beenimmersed for a time sufficient for the desired antimicrobial effect, thefood product can be removed from the bath or flume and the stabilizedcompound can be rinsed, drained, or evaporated off the food product.

In other embodiments, a food product can be treated with a foamingversion a the compound of the present invention. The foam can beprepared by mixing foaming surfactants with the washing solution at timeof use. The foaming surfactants can be nonionic, anionic or cationic innature. Examples of useful surfactant types include, but are not limitedto the following: alcohol ethoxylates, alcohol ethoxylate carboxylate,amine oxides, alkyl sulfates, alkyl ether sulfate, sulfonates,including, for example, alkyl aryl sulfonates, quaternary ammoniumcompounds, alkyl sarcosines, betaines and alkyl amides. The foamingsurfactant is typically mixed at time of use with the washing solution.Use solution levels of the foaming agents is from about 50 ppm to about2.0 wt-%. At time of use, compressed air can be injected into themixture, then applied to the food product surface through a foamapplication device such as a tank foamer or an aspirated wall mountedfoamer.

In some embodiments, a food product can be treated with a thickened orgelled version of a compound of the present invention. In the thickenedor gelled state the washing solution remains in contact with the foodproduct surface for longer periods of time, thus increasing theantimicrobial efficacy. The thickened or gelled solution will alsoadhere to vertical surfaces. The compound or the washing solution can bethickened or gelled using existing technologies such as: xanthan gum,polymeric thickeners, cellulose thickeners, or the like. Rod micelleforming systems such as amine oxides and anionic counter ions could alsobe used. The thickeners or gel forming agents can be used either in theconcentrated product or mixing with the washing solution, at time ofuse. Typical use levels of thickeners or gel agents range from about 100ppm to about 10 wt-%.

Methods for Beverage, Food, and Pharmaceutical Processing

The sulfoperoxycarboxylic acid compounds and compositions of the presentinvention can be used in the manufacture of beverage, food, andpharmaceutical materials including fruit juice, dairy products, maltbeverages, soybean-based products, yogurts, baby foods, bottled waterproducts, teas, cough medicines, drugs, and soft drinks. The compoundsof the present invention can be used to sanitize, disinfect, act as asporicide for, or sterilize bottles, pumps, lines, tanks and mixingequipment used in the manufacture of such beverages. Further, thesulfoperoxycarboxylic acid antimicrobial compounds of the presentinvention can be used in aseptic, cold filling operations in which theinterior of the food, beverage, or pharmaceutical container is sanitizedor sterilized prior to filling. In such operations, a container can becontacted with the sanitizing sulfoperoxycarboxylic acid compound,typically using a spray, dipping, or filling device to intimatelycontact the inside of the container with the sulfoperoxycarboxylic acidcompound, for a sufficient period of time to reduce microorganismpopulations within the container. The container can then be emptied ofthe amount of sanitizer or sterilant used. After emptying, the containercan be rinsed with potable water or sterilized water and again emptied.After rinsing, the container can be filled with the beverage, food, orpharmaceutical. The container can then be sealed, capped or closed andthen packed for shipment for ultimate sale. The sealed container can beautoclaved or retorted for added microorganism kill.

In food, beverage, or pharmaceutical manufacturing, fungalmicroorganisms of the genus Chaetomium or Arthrinium, and spores orbacteria of the genus Bacillus spp. can be a significant problem inbottling processes, particularly in cold aseptic bottling processes. Thesulfoperoxycarboxylic acid compounds of the present invention can beused for the purpose of controlling or substantially reducing (by morethan a 5 log₁₀ reduction) the number of Chaetomium or Arthrinium orBacillus microorganisms in beverage or food or pharmaceutical bottlinglines using cold aseptic bottling techniques.

In such techniques, metallic, aluminum or steel cans can be filled,glass bottles or containers can be filled, or plastic (PET or PBT orPEN) bottles, and the like can be filled using cold aseptic fillingtechniques. In such processes, the sulfoperoxycarboxylic acid materialsof the invention can be used to sanitize the interior of beveragecontainers prior to filling with the carbonated (or noncarbonated)beverage. Typical carbonated beverages in this application include, butare not limited to, cola beverages, fruit beverages, ginger alebeverages, root beer beverages, iced tea beverages which may benon-carbonated, and other common beverages considered soft drinks. Thesulfoperoxycarboxylic acid materials of the invention can be used tosanitize both the tanks, lines, pumps, and other equipment used for themanufacture and storage of the soft drink material and also used in thebottling or containers for the beverages. In an embodiment, thesulfoperoxycarboxylic acid sanitizing materials are useful for killingboth bacterial and fungal microorganisms that can be present on thesurfaces of the production equipment and beverage containers.

The sulfoperoxycarboxylic acid compounds of the present invention caneffectively kill microorganisms (e.g., >1 log₁₀ or up to about 5 log₁₀reduction in 30 seconds) from a concentration level of at least about 50ppm, for example, about 150, about 500 ppm or about 1000 ppm of asulfoperoxycarboxylic acid compound. In an embodiment, thesulfoperoxycarboxylic acid compound, excluding water, would be presentat a concentration of about 0.001 to about 1 wt-%, for example, about0.01 to about 0.15 wt-%, or about 0.05 to about 0.1 wt-%.

All acid, salt, base and other ionic and non-ionic forms of thecompounds described are included as compounds of the invention. Forexample, if a compound is shown as an acid herein, the salt forms of thecompound are also included. Likewise, if a compound is shown as a salt,the acid and/or basic forms are also included.

Those skilled in the art will recognize, or be able to ascertain usingno more than routine experimentation, numerous equivalents to thespecific procedures, embodiments, claims, and examples described herein.Such equivalents are considered to be within the scope of this inventionand covered by the claims appended hereto. The contents of allreferences, patents, and patent applications cited throughout thisapplication are hereby incorporated by reference. The invention isfurther illustrated by the following examples, which should not beconstrued as further limiting.

EXAMPLES

Some of the following Examples were performed using a sulfonatedperoleic acid product. Without wishing to be bound by any particulartheory, it is thought that the peracid formed from a commerciallyavailable sulfonated oleic acid starting material includes a mixture ofthe compounds of the present invention. It is thought that this is due,in part, to the nature of the sulfonated oleic acid starting material.That is, it is thought that because the sulfonated oleic acid startingmaterial is derived from naturally occurring sources, it is notchemically pure, i.e., does not contain only one form of the sulfonatedoleic acid. Thus, without wishing to be bound by any particular theoryit is thought that sulfonated peroleic acid (hereinafter referred to asthe “sulfonated peroleic acid product”) used in these examples includeda mixture of about 20-25 wt % Compound A(10-Hydroxy-9-sulfooctadecaneperoxoic acid) about 20-25 wt % Compound N(10,11-dihydroxy-9-sulfooctadecaneperoxoic acid), about 20-25 wt %Compound I (9-Hydroxy-10-sulfooctadecaneperoxoic acid), and about 20-25wt % Compound O (8,9-dihydroxy-10-sulfooctadecaneperoxoic acid). Theremainder of the peracid composition is thought to include about 5 toabout 10 wt % of a mixture of these compounds.

Example 1 Use of a Sulfoperoxycarboxylic Acid as a Coupler under HighLevel Disinfection Application Conditions

Peroxyoctanoic acid (POOA) stability experiments were performed underhigh level disinfection (HLD) conditions to evaluate the stability of acomposition of the present invention including a sulfonated peroleicacid product, compared with known commercially available disinfectants.

Octave FS®, a peroxyoctanoic containing product, commercially availablefrom Ecolab Inc. was tested against Formulas A, B, and C, and mixturesthereof. Formula A was a mixture of: 2.5 wt % Dequest 2010 (commerciallyavailable from thermphos), peracid grade; 61 wt % hydrogen peroxide(35%); 2.50 wt % sulfuric acid (98%); 6.0 wt % octanoic acid, 19 wt %Hostapur SAS (40%) (commercially available from Clariant); and 9.00 wt %SXS-40 (commercially available from Stepan Company). Formula B was amixture of about 20 wt % of the sulfonated peroleic acid product, about10% peroctanoic acid, about 15 wt % octanoic acid, and about 0.5 wt %hydrogen peroxide. Formula C was a mixture of about 25 wt % of thesulfonated peroleic acid product, and about 0.50 wt % hydrogen peroxide.Mixtures of Formulas A, B, and C were also tested. The test solutionswere diluted with DI water to make a solution with about 1000 ppm POOApresent at a pH of about 6.5. The table below shows the five solutionstested, and the amount of sulfonated peroleic acid product, POOA, andhydrogen peroxide available in ppm in each of the solutions as tested.

TABLE 2 Test solution composition #1 #2 #3 #4 #5 Octave FS ® (wt %)10.00 0 0 0 0 Formula A (wt %) 0 4.2 0 0 0 Formula B (wt %) 0 0 0.880.55 0.33 Formula C (wt %) 0 0 0.22 0.55 0.77 Final weight with added100 100 100 100 100 DI water (g) Sulfonated peroleic acid 0 0 2318 24592554 product (ppm) POOA (ppm) 1000 1000 800 500 300 H₂O₂ 8050 8928 55 5555

The samples were stored at 40° C. and the amount of POOA present wasmeasured by high performance liquid chromatography at the selectedtimes. The following table shows the results of the HPLC analysis of thesamples at various times.

TABLE 3 Test solution 1 2 3 Time POOA POOA POOA 4 5 (hrs) (ppm) (ppm)(ppm) POOA (ppm) POOA (ppm)  0 490 870 700 470 290  6 310 730 590 400250 24 0 120 350 240 150 48 0 10 240 160 100 72 0 0 180 130 80  9 days 00 20 0 0

These results are also graphically depicted in FIG. 1. As can be seenfrom the table above, and FIG. 1, the test solutions including acompound of the present invention, i.e., test solutions 3, 4, and 5,lost less POOA over the course of the first 24 hours compared to theother two test solutions. Even after 48 hours, a greater amount of POOAremained in the test solutions including a compound of the presentinvention, than in the other solutions tested. For each of the testsolutions including a compound of the present invention, it was shownthat the loss of POOA in the solutions was not linear, and that thedecomposition rate of POOA slowed down dramatically at higher ratios ofthe sulfonated peroleic acid product to POOA.

Another stability study was performed to evaluate the stability of acomposition of the present invention at an elevated temperature, i.e.,100° F. A solution including about 2 wt % of the sulfonated peroleicacid product, and about 55 wt % H₂O₂, among other ingredients, was used.The amount of the sulfonated peroleic acid product and H₂O₂ was measuredover the course of 48 days. The results are shown in FIG. 2. As can beseen in this figure, the peracid compound, the sulfonated peroleic acidproduct maintained its activity over the course of the trial, even atthis accelerated temperature.

Yet another stability study was performed to evaluate the stability ofperoxyoctanoic acid when contacted by a compound of the presentinvention, i.e., the sulfonated peroleic acid product, under ambientconditions. For this study, the pH was constant at about 6 to about 6.5.Three different formulas were tested for this study: Formula D includedabout 5 grams of a mixture of the sulfonated peroleic acid product,peroxyoctanoic acid, hydrogen peroxide and sodium cumene sulfate, amongother ingredients; Formula E included about 0.5 g of a mixture of thesulfonated peroleic acid product, and peroxyoctanoic acid; and Formula Fincluded Octave®, commercially available from Ecolab Inc. The amount ofactive peroxyoctanoic acid available at various times over the course of15 days was measured. The results are shown in the table below.

TABLE 4 Formula D Formula E Formula F Time (days) POOA (ppm) POOA (ppm)POOA (ppm) 0 590 640 570 1 550 590 500 4 470 480 360 6 420 400 240 8 410360 160 11 360 270 70 14 310 230 30

These results are also graphically depicted in FIG. 3. As can be seen inthis table, and figure, the formulas including a compound of the presentinvention, i.e., Formulas D and E, retained a higher level of POOA overthe course of 15 days. Thus, without wishing to be bound by anyparticular theory it is thought that the addition of a compositionincluding compounds of the present invention acts to stabilize otherpercarboxylic acids present in the composition.

Example 2 Use of a Sulfoperoxycarboxylic Acid as a Bleaching Agent

The use of a compound of the present invention as a bleaching agent wasevaluated. The soil removal ability of the cleaning composition wasdetermined by washing with artificially soiled fabric swatches. Thesoiled swatches were purchased from a manufacturer or distributor (e.g.Test Fabrics, Inc., West Pittston, Pa.). Soil types such as olive oil,sebum, makeup, wine are characteristic of natural soils found in laundryapplications.

Soiled swatches were washed with the cleaning composition in a devicesuch as a Terg-o-tometer (United States Testing Co., Hoboken, N.J.). TheTerg-o-tometer is a laboratory washing device that consists of multiplepots that reside in a single temperature-controlled water bath, withoverhead agitators under time and speed control. Wash test parametersinclude: wash temperature, wash duration, pH, mechanical agitation, doseof cleaning composition, water hardness, wash formula, and cloth/liquorratio. After completing the appropriate exposure times the fabricsamples were removed. The test chemistries were immediately flushed, andthe swatches rinsed with cold synthetic 5 grain water until 5 cycles offills and rinses were complete. The swatches were then laid flat anddried overnight on white polyester-cotton towels before reflectancereadings were taken using a spectrophotometer, e.g., Hunter ColorQuestXE (reflectance) Spectrophotometer.

To determine the percent (%) soil removal (SR), e.g., bleaching ability,the reflectance of the fabric sample was measured on aspectrophotometer. The “L value” is a direct reading supplied by thespectrophotometer. L generally is indicative of broad visible spectrumreflectance, where a value of 100% would be absolute white. The % soilremoval is calculated from the difference between the initial (beforewashing) lightness (L) value and the final L value (after washing):

SR=((L _(final) −L _(initial))/(96−L _(initial)))×100%

A bleach test was run comparing a composition including a sulfonatedperoleic acid product with the following commercially availablebleaching/cleaning compositions: Ozonit®, and Oxysan® both availablefrom Ecolab Inc. Ozonit® represents a 4.5% peroxyacetic acid productwhile Oxysan® represents a 0.6% peroxyoctanoic acid product. Formula Awas a composition including about 2 wt % of sulfonated peroleic acidproduct, about 5 wt % peroxyacetic acid and about 1.5 wt % ofperoxyoctanoic acid. Formula A was used at a concentration of 1200 ppmand further treated in two of the three cases with additional aceticacid to produce lowered pH test solutions. Ozonit® was used at aconcentration of 2000 ppm. Oxysan® was tested at concentrations of 1272and 2545 ppm. All of the wash solutions were further treated withDetergent MP® and TurboCharge II®, both available from Ecolab Inc andused at 500 and 750 ppm respectively. The bath/wash temperature wasmaintained at 100° F. Detergent MP® and TurboCharge II provide a commonalkaline builder detergent base. The results from the bleaching test areshown in the table below.

TABLE 5 Stain Removal (%) from Conc. of Cotton Bleach Bleach Type TeaRed Wine Ketchup (mg/L) pH Ozonit ® 29 59 27 2000 9.50 Oxysan ® 21 66 191272 8.00 2X Oxysan ® 33 69 27 2545 8.00 Formula A, pH 8.0 37 73 38 10008.00 Formula A, pH 8.5 38 72 41 1000 8.50 Formula A, pH 9.0 34 69 361000 9.00

As can be seen from this table, the compositions of Formula A achieved ahigher percent stain removal than the commercially available solutionstested at all pH levels tested, especially in the cases of ketchup whichrepresents a hydrophobic stain.

Formula A was also tested using a full scale Wash Wheel Bleach Test. Thetest was run with a commercial 35 lb side loading washing machine(UniMac UX35PVXR). Multipaneled pre-stained test sheets (Ecomon No. 1 &Ecomon No.4 included 14 bleachable and 12 pigment/unbleachable stainedpanels) were added to the otherwise empty machine before initiating a 20minute washing program (typically at 40° C.). The chemistries were addedin a 30 second staggered sequence via the overhead dispensing cups oncethe machine was filled with 48 L of 5 grain synthetic soft water. Theinitial chemistry added was the alkaline detergent product (about 84 gof Turboemulsion, commercially available from Ecolab Inc.). Thebleaching chemistry was then added ˜30 seconds after thesurfactant-caustic blend and a 20 minute wash cycle was begun. After thewash cycle the machine was drained and 3 rinse cycles were executed. Thesheets were retrieved and air dried at 70° F., overnight beforemeasuring each swatch panel's reflectance with a Hunter ColorQuest XE(reflectance) Spectrophotometer (UV filter “IN”). The results are shownin the table below.

TABLE 6 L Reflectance Values ⁵Stain Initial Removal, % stained³Turboemulsion TE + TE + TE + TE + swatch only ⁶Formula A ⁴OzonitFormula A Ozonit Bleachable Stains Tea on CO 80.64 80.67 91.62 88.9471.48 54.01 Tea on PES/CO 80.43 79.24 91.17 88.28 68.96 50.40 Red Wineon CO 73.66 85.94 93.03 92.06 86.72 82.36 Red Wine on PES/CO, aged 73.8282.98 91.71 90.67 80.67 75.97 Coffee on CO 78.92 90.72 93.10 92.70 83.0480.70 Coffee on PES/CO 79.77 92.27 93.62 93.28 85.34 83.26 Black currantjuice on CO 64.40 88.37 93.54 92.82 92.22 89.94 Black currant juice on63.57 85.02 93.30 92.07 91.68 87.89 PES/CO Blood on CO IEC 456, aged46.25 89.51 90.60 91.48 89.14 90.91 Blood on CO IEC 456, not 49.36 93.0693.81 93.88 95.30 95.45 aged Blood/Milk/Ink on CO 45.26 61.00 51.1051.89 11.51 13.06 Cocoa on CO IEC 456, not 75.22 83.76 83.47 83.27 39.7238.74 aged Blood/Milk/Soot on CO 58.87 86.37 69.87 70.54 29.62 31.44Egg/Soot on CO 62.87 76.36 76.09 75.81 39.89 39.05 average/14 66.6583.95 86.15 85.55 68.95 65.23 Unbleachable Stains Pigment/Lanolin on CO71.98 80.90 78.63 80.55 27.70 35.68 Pigment/Lanolin on PES/ 66.65 82.3873.28 81.72 22.60 51.35 CO Pigment/Sebum on CO 73.19 87.70 84.02 86.7647.49 59.48 Pigment/Sebum on PES/ 70.64 87.97 77.82 86.74 28.33 63.49 COSoot/Olive Oil on CO 47.93 69.90 62.45 64.87 30.21 35.23 Soot/Olive Oilon PES/CO 40.77 62.89 56.23 58.57 27.99 32.23 Soot/Mineral Oil on CO59.76 72.35 68.93 71.80 25.30 33.21 Soot/Mineral Oil on PES/ 55.62 80.1573.89 78.78 45.25 57.36 CO Used Motor Oil on CO 65.91 73.06 70.99 71.7716.89 19.47 Used Motor Oil on PES/CO 61.10 68.27 64.08 66.01 8.53 14.08Makeup on CO 84.81 90.06 89.50 90.14 41.94 47.63 Makeup on PES/CO 85.1692.57 91.91 92.14 62.24 64.42 average/12 70.85 86.01 81.49 84.62 32.0442.80 Notes: ³Turboemulsion (TE) is a commercially available all-in-oneemulsion of alkaline metal chelators emulsified with a surfactant blendmade by Ecolab, Inc. and was used in this test at 1750 ppm. ⁴Ozonit is aPeracetic acid-Hydrogen peroxide bleach disinfectant used at aconcentration of 2000 ppm. Ozonit is a blend of Peracetic acid andHydrogen peroxide made by Ecolab, Inc.. ⁵The “Stain Removal, %” wascalculated using the following formula: SR = ((Lfinal − Lintial)/(96 −Lintial)) × 100% CO: Cotton; PES/CO: Polyester-Cotton blend

As can be seen from this table, Formula A averages superior bleaching toOzonit®. Although the superiority on these “bleachable” stains is only3.7 points (5.4%), on those stains which better resist wash removal e.g.tea, the difference was as many as 17 points (24%) higher.

Another full scale wash testing was conducted using a wash wheel (fullsize side loading washing machine), but rather than individual soiledswatches this test utilized multipaneled sheets combining 14“bleachable” stained swatches (Ecomon 4) and a second sheet whichcombined 12 “unbleachable” pigment/hydrocarbon stained swatches (Ecomon1). These panels are custom made for Ecolab by wfk Testgewebe Gmbh ofBruggen, Germany. This extensive bleach test utilized a designexperiment which varied concentrations sometimes simultaneously withtemperatures etc. Following completion of the specified wash time, allEcomon sheets were rinsed thoroughly, dried and their broad spectrumlight reflectivities were measured, again with UV filtering to removalpossible interference from optical brightener effects. Unlike thetergotometer data, the % stain removal wasn't calculated but was ratherdirectly measured from the reflectance instrument (Minolta CM-2610dSpektrophotometer). A “Y” value representing broad spectrum reflectivitywas reported. The higher the “Y” value, the whiter the material, andtherefore, the greater the bleaching or stain removal.

In this test, Formula A was compared to Ozonit®, Ozonit Super® (a 15%peroxyacetic acid product available from Ecolab) and Oxysan® these werevariously combined with the following commercially availablealkaline-builder cleaning agents: Triplex Emulsion®, available fromEcolab Inc.; Turbo Usona®, available from Ecolab Inc.; Ozonit Super®,available from Ecolab Inc.; and Oxysan®, available from Ecolab Inc. Theresults are shown in the tables below.

TABLE 7 Bleaching Results Black Black Currant Tea Tea Red Wine Red WineCoffee Coffee Currant Juice on on on CO on PES/CO on on Juice onProcedure CO PES/CO aged aged CO PES/CO on CO PES/CO Ave. 1.5 ml/l 72.770.0 75.4 74.6 80.2 84.6 82.5 84.1 78.0 ²Triplex Emulsion + 1 ml/lFormula A Conditions: 15′ 40° C. 1.5 ml/l 80.6 79.6 82.5 80.5 83.5 86.085.5 86.1 83.0 Triplex Emulsion + 2 ml/l Formula A Conditions: 15′ 40°C. 1.5 ml/l 82.6 83.1 84.3 80.9 84.3 86.0 86.2 86.3 84.2 TriplexEmulsion + 2.5 ml/l Formula A Conditions: 20′ 40° C. 1.5 ml/l 78.5 79.082.2 82.1 84.8 86.2 86.7 86.5 83.3 Triplex Emulsion + 1 ml/l OzonitSuper Conditions: 10′ 70° C. 4 ml/l ³Turbo 80.8 80.5 81.5 79.0 81.1 84.282.0 80.8 81.2 Usona + 2 ml/l ⁴Ozonit Performance Conditions: 20′ 40° C.4 ml/l Turbo 79.2 77.9 78.9 76.3 79.9 83.3 77.6 75.9 78.6 Usona + 4 ml/l⁵Oxysan Conditions: 20′ 40° C. 4 ml/l Turbo 82.2 81.7 82.1 80.5 82.685.2 82.6 82.6 82.4 Usona + 2 ml/l Formula A Conditions: 15′ 40° C. LSD1.8 3 1.9 2.4 1.1 0.8 1.7 1.8 1.9

TABLE 8 Bleaching results 1.5 ml/l 4 ml/l 1.5 ml/l 1.5 ml/l 1.5 ml/lTriplex ³Turbo 4 ml/l 4 ml/l ²Triplex Triplex Triplex Emulsion + Usona +Turbo Turbo Emulsion + Emulsion + Emulsion + 1 ml/l 2 ml/l Usona +Usona + 1 ml/l 2 ml/l 2.5 ml/l Ozonit ⁴Ozonit 4 ml/l 2 ml/l Formula AFormula A Formula A Super Performance ⁵Oxysan Formula A Conditions:Conditions: Conditions: Conditions: Conditions: Conditions: Conditions:15′ 40° C. 15′ 40° C. 20′ 40° C. 10′ 70° C. 20′ 40° C. 20′ 40° C. 15′40° C. LSD Pigment/ 54.3 55.6 56.8 67.3 57.5 56.6 54.8 6.1 Lanolin on COPigment/ 53.4 51.4 48.8 60.6 46.1 44.9 46.2 5.8 Lanolin on PES/COPigment/ 68.3 59.7 59.6 67.5 60.1 58.0 60.9 6.7 Sebum on CO Pigment/66.0 54.2 54.7 73.4 53.2 50.5 54.3 6.3 Sebum on PES/CO Soot/ 47.7 42.532.2 46.9 24.7 25.1 24.3 7.8 Olive Oil on CO Soot/ 33.8 28.5 24.2 38.415.7 14.4 13.0 9.6 Olive Oil on PES/CO Soot/ 36.9 34.3 36.0 34.0 33.430.6 30.6 4.5 Min. Oil on CO Soot/ 42.4 43.9 35.8 46.6 31.0 32.7 37.78.2 Min. Oil on PES/CO Used 42.7 43.9 42.6 46.0 44.0 44.9 46.3 2.6 MotorOil on CO Used 37.7 34.7 33.7 36.4 32.2 33.5 33.8 1.6 Motor Oil onPES/CO Make 75.3 74.1 75.7 84.1 73.3 72.4 73.5 4 up on CO Make 79.8 77.976.8 86.6 75.7 74.0 76.9 3.8 up on PES/CO Lipstick 87.6 87.4 87.3 87.785.9 86.9 87.3 1.4 on Co Lipstick 3.0470618 on PES/CO Average 53.2 50.148.1 57.3 45.6 44.8 46.0 5.6 Notes: 1. Y-value refers to a reflectancevalue calculated by the Minolta CM-2610d Spektrophotometer. It is verysimilar to the L-value calculated by the Hunter Lab'sSpectrophotometers. ²Triplex Emulsion is a commercially availableall-in-one emulsion of alkaline metal chelators emulsified with asurfactant blend made by Ecolab, Inc. (Europe). ³Turbo Usona is acommercially available all-in-one emulsion of alkaline metal chelatorsemulsified with a surfactant blend made by Ecolab, Inc. (Europe).⁴Ozonit Super is a Peracetic acid-Hydrogen peroxide bleach disinfectant,made by Ecolab, Inc. (Europe). ⁵Oxysan is a Peracetic acid-Hydrogenperoxide bleach disinfectant which also contains Peroxyoctanoic acid,and is made by Ecolab, Inc. (Europe). CO: Cotton PES/CO:Polyester-Cotton blend

As can be seen from these results, overall the samples washed withcompositions of the present invention, i.e., Formula A, achieved similarbleaching compared with commercially available bleaching agents.

Example 3 Use of a Sulfoperoxycarboxylic Acid as a Bleaching Agent

A bleach test was run comparing a composition including asulfoperoxycarboxylic acid of the present invention, i.e.,11-sulfoundecaneperoxoic acid (Compound D) with the followingcommercially available bleaching/cleaning compositions: Tsunami 100®,available from Ecolab Inc.; Oxonia Active®, available from Ecolab Inc.;hydrogen peroxide (35%); and PAP-70®, available from Solvay. Thesechemistries were used as is except for pH adjustments to pH 8 usingsodium bicarbonate, and pH 12 by the addition of sodium hydroxide, in 5grain hardwater.

Fabric swatches soiled with tea, blood, or wine were used for thisexample. The soil swatches were washed using the same experimentalprocedure described above in Example 2. However, for this example, thesoil swatches were washed for 10 minutes at 120° F. The pH of the washsolution for all samples was about 9. The percent soil removal (SR) wasdetermined according to the method described above in Example 2. Thefollowing table shows the results of this study.

TABLE 9 Use Solution Wash Bleach Available Time mg/L use Oxygen BleachType pH Temp (F.) (min) % SR solution (ppm) Removal of Tea StainsComposition 9 120 10 37 1350 56 Including Compound D Tsunami 9 120 10 34770 56 100 ® Oxonia 9 120 10 27 410 56 Active ® H₂O₂ (35%) 9 120 10 24340 56 PAP-70 9 120 10 63 1386 56 Water 9 120 10 11 0 56 (control)Removal of Blood Stains Composition 9 120 10 90 1350 56 IncludingCompound D Tsunami 9 120 10 81 770 56 100 ® Oxonia 9 120 10 80 410 56Active ® H₂O₂ (35%) 9 120 10 82 340 56 PAP-70 9 120 10 88 1386 56 Water9 120 10 36 0 0 (control) Removal of Red Wine Stains Composition 9 12010 62 1350 56 including Compound D Tsunami 9 120 10 57 770 56 100 ®Oxonia 9 120 10 41 410 56 Active ® H₂O₂ (35%) 9 120 10 45 340 56 PAP-709 120 10 74 1386 56 Water 9 120 10 36 0 56 (control)

As can be seen from this table, with respect to tea stains, the PAP-70®composition achieved the greatest soil removal. The compositioncontaining a compound of the present invention achieved the next highestpercent soil removal. With respect to blood stains, the compositioncontaining the sulfoperoxycarboxylic acid of the present inventionachieved the greatest soil removal. However, all concentrated oxidizersperformed well in removing the blood stains. With respect to the redwine stains, the sulfoperoxycarboxylic acid of the present inventionperformed well compared to the PAP-70®.

Example 4 Stability Studies

The stability of a sulfoperoxycarboxylic acid of the present invention,i.e., 11-sulfoundecaneperoxoic acid (Compound D), was compared to thatof phthalimidoperoxyhexanoic acid (PAP). The stability data for the PAPsample were taken from U.S. Pat. No. 5,994,284, assigned to ClariantGmbH. Samples of the compound of the present invention were stored forfour (4) weeks at various temperatures. The loss of active oxygen wasmeasured by titrimetry. The results are shown in the table below.

TABLE 10 Storage Time Loss of Active Compound (weeks) Temperature (° C.)Oxygen (%) Compound D 4 Room Temp. 0.78 Compound D 4 38 7.9 Compound D 450 15.7 PAP 4 25 1.4 PAP 4 40 2.0 PAP 4 50 12.0

As can be seen from this table, the compound of the present inventionwas more stable, i.e., lost less active oxygen, at room temperature,i.e., about 23° C., than the PAP at 25° C.

Example 5 Bleaching Performance of Various Formulas of the PresentInvention

A test was run to compare the bleaching properties of compositions ofthe present invention with the following commercially availablebleaching agents: Ozonit®, available from Ecolab Inc.; and PAP®,available from Clariant. The following compositions of the presentinvention were used: Formula A, which included about 25 wt % of thesulfonated peroleic acid product, about 70 wt % H₂O₂ (35%), and about 5wt % HEDP 60; Formula B which included about 24 wt % of a mixture of thesulfonated peroleic acid product and peroxyoctanoic acid, about 72 wt %H₂O₂ (35%), and about 4 wt % HEDP 60; and Formula C which included about20 wt % of a mixture of the sulfonated peroleic acid product andperoxyoctanoic acid, about 62 wt % H₂O₂ (35%), about 4 wt % HEDP 60, andabout 13 wt % acetic acid. These formulas were compared with thecommercially available bleaching agents at 40° C. at a pH of between 7to 8. The Ozonit® was also tested at 60° C.

To measure the bleaching ability of the formulations, a bleaching testas described in Example 2 was performed. The results are shown in FIG.4. As can be seen in this figure, Formulas A, B and C had far superiorbleaching ability compared to Ozonit® at 40° C. When the Ozonit® wasused at 60° C., Formulas A, B, and C had very similar bleaching ability.Formula C also had similar bleaching performance compared to the PAP.Thus, Formulas A, B, and C showed equal, if not better, bleachingproperties compared to known commercially available bleaching agents at40° C.

Example 6 Antimicrobial Studies

(a) Bactericidal Efficacy

An experiment was performed to determine the bactericidal efficacy of acomposition according to the present invention, with and without asurfactant, as compared to other commercially available products.Formula A included about 1190 ppm of a sulfonated peroleic acid product,as well as peroxyoctanoic acid, and peracetic acid. The surfactant usedfor this example was Turboemulsion® (TE), commercially available fromEcolab Inc. The compositions were tested against Clostridium difficileATCC 9689, MRSA ATCC 33592, Enterococcus hirae ATCC 10541, Escheria coliATCC 11229, and Pseudomonas aeruginosa ATCC 15442, at 5 and 60 minuteexposure times. The commercially available compositions, Ozonit®, andPAP were also tested. The following formulations were tested:

TABLE 11 Desired Test Use Solution Concentration (Volume of Test Test ofSubstance/Total Formulation Active Agent Diluent Volume) pH Formula A1190 ppm Sterile 0.194 g Formula A + 7.59 with surfactant MilliQ 170 μLTE/100 g Water Formula A 1190 ppm 0.194 g Formula A/ 8.53 without 100 gSurfactant PAP ® 1820 ppm 0.182 g PAP + 1.5 g 8.50 TE/100 g Ozonit ®2000 0.200 g Ozonit + 7.21 1.5 g TE/100 g

The test method followed was according to European Standard EN 13704:Quantitative Suspension Test for the Evaluation of Sporicidal Activityof Chemical Disinfectants and Antiseptics Used in Food, Industrial,Domestic and Institutional Areas. Generally, a test suspension ofbacterial spores in a solution of interfering substance, simulatingclean conditions, was added to a prepared sample of the test formulationdiluted in hard water. The mixture was maintained at the specifictemperature and time desired. At this contact time, an aliquot is taken;the sporicidal action in this portion was immediately neutralized orsuppressed by a validated method. The number of surviving bacterialspores in each sample was determined and the reduction in viable countswas calculated.

The disinfectant properties of each of the formulations at 5 minutes at40° C. is shown below in Table 12.

TABLE 12 Formula A Formula A with without Test/System Surfactant PAPOzonit Surfactant MRSA >6.66 >6.66 >6.66 >6.66Enterococcus >6.26 >6.26 >6.26 >6.26 hirae ATCC 10541Escherichia >6.74 >6.74 >6.74 >6.74 coli ATCC 11229Pseudomonas >6.32 >6.32 >6.32 >6.32 aeruginosa ATCC 15442Clostridium >3.87 1.17 2.57 3.09 difficile ATCC 9689

As can be seen from this table, the compositions of the presentinvention that were tested were as effective as a disinfectant as thecommercially available formulations tested. Further, with respect toClostridium difficile, the compositions of the present invention weremore effective than the commercially available products tested.

(b) Stability and Sporicidal Efficacy at 14 Days

A test was run to determine the stability and sporicidal efficacy of acomposition of the present invention against spores. The compositiontested included the sulfonated peroleic acid product, and an amount ofperoxyoctanoic acid. The test method used was the European Standard EN13704: Quantitative Suspension Test for the Evaluation of SporicidalActivity of Chemical Disinfectants and Antiseptics Used in Food,Industrial Domestic and Institutional Areas, described above. The tablebelow shows the results of this study.

TABLE 13 Sulfonated Peroleic Acid Product + POOA (14 Day Retention) DIWater pH 6.5 B. subtilis C. difficile Clean Conditions 20° C. 60 min 60min Log reduction 3.84 Log reduction 2.71

A composition including 30 ppm peroxyoctanoic acid was also tested. Thecomposition of peroxyoctanoic acid alone did not result in a reduction.

FIG. 5 shows the stability impact that the compound of the presentinvention used, i.e., the sulfonated peroleic acid product, had on theamount of POOA over time during this study. As can be seen from thisfigure, the amount of POOA available over time was higher with thesample of POOA that was stabilized using a composition of the presentinvention, compared to a sample of POOA that was not stabilized using acomposition of the present invention.

(c) Synergistic Effect of a Composition of the Present Invention with aKnown Sanitizer

For this study, the ASME 1052-96: Standard Test Method for Efficacy ofAntimicrobial Agents against Viruses in Suspension was used. Acomposition including 1000 ppm peroxyacetic acid (POAA) was testedalone, and in combination with sulfonated peroleic acid product.

The POAA solution alone did not display complete inactivation ofPoliovirus Type 1 after an exposure time of four minutes. The reductionsin viral titer were ≦0.75 and ≦0.50 log 10. When the POAA solution wastested with 1000 ppm of the sulfonated peroleic acid product, thesolution displayed complete inactivation of Poliovirus Type 1 after anexposure time of a few minutes, and was therefore efficacious againstthe virus. The reduction in viral titer was ≧5.75 log10.

(d) Synergistic Effect of a Compound of the Present Invention withPeroxyoctanoic Acid

For this study, the MS103: Quantitative Tuberculocidal Test was used.The sulfonated peroleic acid product was tested alone, and incombination with peroxyoctanoic acid at various concentrations againstMycobacterium bovis BCG. The compositions were tested at a pH of 6.5 atroom temperature. The results are shown in the table below.

TABLE 14 Test Substance Exposure Time Log Reduction 1000 ppm SulfonatedPeroleic 2.5 min 4.46 Acid Product   5 min 5.11 300 ppm POOA 2.5 min3.48   5 min <4.31 1000 ppm Sulfonated Peroleic 2.5 min >7.31 AcidProduct and   5 min >7.31 300 ppm POOA 1000 ppm Sulfonated Peroleic 2.5min ≧7.31 Acid Product and   5 min >7.31 150 ppm POOA

As can be seen from this table, the samples treated with both acomposition of the present invention including the sulfonated peroleicacid product, and POOA had a higher log reduction of Mycobacterium bovisBCG than those samples treated with either the sulfonated peroleic acidproduct or POOA alone. Although it was found that the samples treatedwith just the sulfonated peroleic acid product did have a higher logreduction of bacteria than the samples treated with just POOA.

(e) Use of a Compound of the Invention as a Hospital Disinfectant

For this test, the AOAC Official Method 955.15—Testing DisinfectantAgainst Staphylococcus aureus and the AOAC Official Method964.02—Testing Disinfectants Against Pseudomonas aeruginosa were used.The composition used included the sulfonated peroleic acid product, andperoxyoctanoic acid (POOA), at various concentrations. The followingchart summarizes the test procedure used, and the results.

TABLE 15 Test Desired Dilution Substance Concentration Diluent (Volumeof Test System/Total Volume) Test pH Sulfonated 1000 ppm 400 ppm 2.910 gSulfonated Peroleic Acid Product + 6.5 Peroleic Sulfonated Synthetic0.2345 g POOA/1500 g Acid Peroleic Acid Hard Product + Product WaterPOOA 300 ppm POOA 1000 ppm 0.1852 g Sulfonated Peroleic Acid Product +6.5 Sulfonated 0.4690 g POOA/1500 g Peroleic Acid Product 150 ppm POOA #Negative Tubes/ Test system Test Substance # Carriers TestedStaphylococcus aureus 1000 ppm Sulfonated Peroleic Acid 60/60 ATCC 6538Product + 300 ppm POOA Staphylococcus aureus 1000 ppm SulfonatedPeroleic Acid 60/60 ATCC 6538 Product + 150 ppm POOA Pseudomonasaeruginosa 1000 ppm Sulfonated Peroleic Acid 60/60 ATCC 15442 Product +300 ppm POOA Pseudomonas aeruginosa 1000 ppm Sulfonated Peroleic Acid60/60 ATCC 15442 Product + 150 ppm POOA

As can be seen from this table, the compositions tested were effectiveagainst each of the test systems.

Example 7 Coupling Abilities of Compounds of the Present Invention

The ability of a composition of the present invention including thesulfonated peroleic acid product to couple octanoic acid was compared tothe coupling abilities of two known commercially available couplingagents, NAS and linear alkylbenzene sulphonate (LAS).

The results can be seen in FIG. 6. As can be seen from this figure, onegram of the sulfonated peroleic acid product was able to couple twice asmuch octanoic acid compared to the other coupling agents tested.

Example 8 Formation of Sulfonated Carboxylic Acids and theirPercarboxylic Salts

A study was run to determine the effect of the position of the sulfonategroup on the carboxylic acid in forming a peracid. Specifically, a studywas run to determine whether having the sulfonate group at the aposition prohibits the oxidation and/or perhydrolysis of the carboxylicacid group to form the corresponding peroxycarboxylic acid.

Commercially available sulfonated fatty acid salts (methyl esters) arepredominantly a sulfonated, including, for example, Alpha-Step PC-48(commercially available from the Stepan Comp.), Alpha-Step MC-48(MC-48)(commercially available from the Stepan Comp.), Alpha-Step BSS-45(commercially available from the Stepan Comp.), and MES (commerciallyavailable from the Lion Corporation). Structurally, these compounds aresodium alphasulfo methyl C₁₂-C₁₈ esters and disodium alphasulfo C₁₂-C₁₈fatty acid salts. Their structures are shown below:

Sulfonated oleic acid is another commercially available sulfonated fattyacid. These compounds are mainly 8-sulfo-octadecenoic acid salts, with aminority of 9-sulfo-10-hydroxy-octadecanoic acid salts. They are notsulfonated at the a position. The structures of these types of compoundsare shown below:

α-sulfonated fatty acids were prepared by the hydrolysis of the mixtureof α-sulfonated fatty acid methyl ester and the acid (MC-48). To abeaker containing 25 g of MC-48, 12 g of 50% NaOH solution was added.The mixture was stirred at ambient temperatures for 3 hours. The mixturewas then acidified by adding H₂SO₄ (50%) until the pH of the mixturereached about 0-1. The white solid precipitate was filtered, washed withcold water, and dried. The white solid powder yield was evaluated using¹³C NMR (DMSO-d₆). The methyl group of the methyl ester in the rawmaterial was not observed, indicating complete hydrolysis.

In order to try and form the peracid using an acid catalyzed hydroxidereaction the following reaction was performed. 0.5 g of the MC-48derived fatty acid sulfonate, as prepared above, was weighed into a 50ml beaker. To this beaker, 30 g of H₂O₂ (35%) was added. then, 5 g ofH₂SO₄ (985) was slowly added, producing a clear solution. After sittingat 50° C. for 24 hours, the solution was analyzed to determine thepresence of a peracid.

To determine the presence of a peracid, a kinetic iodometric titrationsimilar to the method disclosed in Sully and Williams (“The Analysis ofPer-Acids and Hydrogen Peroxide,” The Analyst, 87:1037, p. 653 (August1962)) was used. This method has demonstrated a lower detection limit ofabout 0.3 ppm for POAA. Given the molecular weight ratio of POAA to theperspective percarboxylic acid of PC-48, the detection limit wasestimated to be about 1.4 ppm (3.93×10⁻⁶ M). No peracid formation wasobserved. This is equivalent to a percarboxylic acid formation constant(Keq) less than 0.002, suggesting substantially no peracid was formed.

Alternatively, formation of the peracid was determined using ¹³C NMR(D₂0). Using this technique, no carbonyl resonance signal from theperacid was observed.

Other α-sulfonated fatty acid sources such as Alpha-Step PC-48 andAlpha-Step BSS-45 were also reacted with H₂O₂ in a similar manner, andin both cases, no corresponding peracids were detected.

Non-α-sulfonated fatty acids were also tested to determine thelikelihood of peracid formation. For the sulfonated oleic acid discussedabove, the measured formation constant was 1.42. The sulfonatedundecenoic acid was collected as a stable solid powder, so the formationconstant was not measured. Although the formation constant of theperacid of sulfonated oleic acid is significantly lower than that of themost common commercialized peracid, peroxyacetic acid (Keq=2.70), it isstill high enough to make practical yields.

Overall, without wishing to be bound by any particular theory, it isthought that the α-sulfo group prohibits the oxidation and/orperhydrolysis of the carboxylic acid group by H₂O₂ to the correspondingperacid. This may in part be due to its strong electron withdrawingeffects.

Example 9 Clean in Place Sanitizing Compositions

A study was run to determine the efficacy of compositions of the presentinvention as sanitizers used in a clean in place cleaning method. Acomposition including about 5.85 wt % of the sulfonated peroleic acidproduct, and about 11.6% hydrogen peroxide, about 1 wt % of a chelatingagent, about 12.75 wt % of H₂SO₄, about 13.6 wt % NAS-FAL (sodium octanesulfonate), and about 1.5 wt % of SXS (commercially available from theStepan Company) was prepared. Synthetic hard water was used to dilutethe test composition to the desired peracid concentration. The peracidwas tested at concentrations of 1000 ppm, 750 ppm and 500 ppm. The pH ofthe use solutions were as follows:

Concentration of Peracid in Use Solution pH  500 ppm peracid 1.65  750ppm 1.46 1000 ppm 1.38

The use solutions were tested against Staphylococcus aureus ATCC 6538and Pseudomonas aeruginosa ATCC 15442. The organic soil used was 5%Fetal Bovine Serum. The exposure time of the test was 5 minutes at atemperature of 20±1° C. A neutralizer screen was also performed as partof the testing to verify that the neutralizer adequately neutralized theproduct and was not detrimental to the tested organisms. The plates wereincubated at 35° C. for 48 hours with the test systems prior to exposureto the peracids. The results are shown in the table below.

TABLE 16 Staphylococcus aureus ATCC 6538 Test Substance # NegativeTubes/# Carriers Tested 1000 ppm Peracid Composition 60/60 Pseudomonasaeruginosa ATCC 15442 Test Substance # Negative Tubes/# Carriers Tested1000 ppm Peracid Composition 60/60 Test Controls Control Test SystemResults Negative Carrier 1 negative of 1 tested Positive CarrierStaphylococcus aureus ATCC 6538 1 positive of 1 tested Positive CarrierPseudomonas aeruginosa ATCC 15442 1 positive of 1 tested Organic Soil 1negative of 1 tested Neutralization (1000 ppm) Staphylococcus aureusATCC 6538 6 positive of 6 tested Neutralization (1000 ppm) Pseudomonasaeruginosa ATCC 15442 6 positive of 6 tested Culture EnumerationStaphylococcus aureus ATCC 6538 9.0 × 10⁸ CFU/mL Culture EnumerationPseudomonas aeruginosa ATCC 15442 1.0 × 10⁹ CFU/mL Carrier EnumerationStaphylococcus aureus ATCC 6538 1.0 × 10⁶ CFU/mL 1.0 × 10⁷ CFU/CarrierCarrier Enumeration Pseudomonas aeruginosa ATCC 15442 2.3 × 10⁶ CFU/mL2.3 × 10⁷ CFU/Carrier Staphylococcus aureus ATCC 6538 Test Substance #Negative Tubes/# Carriers Tested 500 ppm Peracid Composition 59/60 750ppm Peracid Composition 60/60 Pseudomonas aeruginosa ATCC 15442 TestSubstance # Negative Tubes/# Carriers Tested 500 ppm Peracid Composition58/60 750 ppm Peracid Composition 60/60 Test Controls Control TestSystem Results Negative Carrier 1 negative of 1 tested Positive CarrierStaphylococcus aureus ATCC 6538 1 positive of 1 tested Positive CarrierPseudomonas aeruginosa ATCC 15442 1 positive of 1 tested Organic Soil 1negative of 1 tested Neutralization Staphylococcus aureus ATCC 6538 3positive of 3 tested Neutralization Pseudomonas aeruginosa ATCC 15442 3positive of 3 tested Culture Enumeration Staphylococcus aureus ATCC 65381.0 × 10⁹ CFU/mL Culture Enumeration Pseudomonas aeruginosa ATCC 154421.0 × 10⁹ CFU/mL Carrier Enumeration Staphylococcus aureus ATCC 6538 7.2× 10⁵ CFU/mL 7.2 × 10⁶ CFU/Carrier Carrier Enumeration Pseudomonasaeruginosa ATCC 15442 2.0 × 10⁶ CFU/mL 2.0 × 10⁷ CFU/Carrier

As can be seen from these results, the use solutions tested wereeffective disinfectants against both Staphylococcus aureus, andPseudomonas aeruginosa at the concentrations tested.

Another study was run to determine the sanitizing efficacy of the testsolution against Staphylococcus aureus ATCC 6538 and Escherichia coliATCC 11229 after a 30 second exposure time. For this experiment thesolutions were diluted to have a concentration of 50 ppm, 75 ppm or 100ppm of the sulfonated peroleic acid product. The pH of the use solutionswere as follows:

Concentration of Peracid in Use Solution pH  50 ppm peracid 2.70  75 ppm2.47 100 ppm 2.30

The use solutions were tested against Staphylococcus aureus ATCC 6538and Escherichia coli ATCC 11229. The exposure time was 30 seconds at atemperature of 25±1° C. A neutralizer screen was also performed as partof the testing to verify that the neutralizer adequately neutralized theproduct and was not detrimental to the tested organisms. The plates wereincubated at 35° C. for 48 hours with the test systems prior to exposureto the peracids. The results are shown in the table below.

TABLE 17 Inoculum Numbers Average Log₁₀ Test System CFU/mL Log₁₀ GrowthGrowth Staphylococcus aureus 107 × 10⁶, 109 × 10⁶ 8.03, 8.04 8.04 ATCC6538 Escherichia coli 138 × 10⁶, 151 × 10⁶ 8.14, 8.18 8.16 ATCC 11229Staphylococcus aureus ATCC 6538 Survivors Average Log₁₀ Test Substance(CFU/mL) Log₁₀ Growth Growth Log Reduction 50 ppm Peracid 28 × 10¹, 20 ×10¹ 2.45, 2.30 2.38 5.66 Composition 75 ppm Peracid  0 × 10¹, 100 × 10¹<1.00, 3.00   <2.00 >6.04 Composition 100 ppm Peracid  0 × 10¹, 0 × 10¹<1.00, <1.00 <1.00 >7.04 Composition Escherichia coli ATCC 11229Survivors Average Log₁₀ Test Substance (CFU/mL) Log₁₀ Growth Growth LogReduction 50 ppm Peracid 0 × 10¹, 2 × 10¹ <1.00, 1.30   <1.15 >7.01Composition 75 ppm Peracid 0 × 10¹, 0 × 10¹ <1.00, <1.00 <1.00 >7.16Composition 100 ppm Peracid 0 × 10¹, 0 × 10¹ <1.00, <1.00 <1.00 >7.16Composition

As can be seen from these results the use solutions tested wereeffective sanitizers against both Staphylococcus aureus and Escherichiacoli. The test solution containing 100 ppm of the sulfonated peroleicacid product was the most effective sanitizer.

Example 10 Foam Properties of Selected Compositions of the PresentInvention

A study was performed to determine the foam properties of selectedcompositions of the present invention, compared to compositionsincluding commercially available surfactants. The following compositionswere prepared: Formula A included 50 ppm of the sulfonated peroleic acidproduct at a pH of 2.48; Formula B included 50 ppm of the sulfonatedperoleic acid product at a pH6.75; Formula C included 64 ppm of acommercially available sulfonated oleic acid (SOA)(Lankropol OPA (50%)available from Akzo Nobel) at a pH of 2.48; Formula D included 64 ppm ofa commercially available sulfonated oleic acid (Lankropol OPA (50%)available from Akzo Nobel) at a pH of 6.56; Formula E included 128 ppmof a commercially available sulfonated oleic acid (Lankropol OPA (50%)available from Akzo Nobel) at a pH of 2.48; Formula F included 128 ppmof a commercially available sulfonated oleic acid (Lankropol OPA (50%)available from Akzo Nobel) at a pH of 7.20; and Formula G included 93ppm of sodium octane sulfonate (NAS) (commercially available fromEcolab) at a pH of 2.48. The foam heights were determined using thefollowing method. First 3000 ml of each formula was prepared and gentlypoured into Glewwe cylinder. A ruler was attached to the side of thecylinder, and the solution was level with the bottom of the ruler. Thepump was turned on. Foam height was estimated by reading the averagelevel of foaming according to the ruler. Foam height readings were takenversus time with a stopwatch or timer. The pump was turned off andheight of the foam was recorded at various times. The results are shownin the table below.

TABLE 18 Pump On Time (sec) Pump Off Time (sec) 30 60 300 30 60 300 FoamFoam Foam Foam Foam Foam Height Height Height Height Height HeightSample (inches) (inches) (inches) (inches) (inches) (inches) Formula A2.5 3.8 5.5 3.5 2.0 0.5 Formula B 1.5 2.0 2.5 0.2 <0.1 NA Formula C 4.06.2 9.2 8.7 8.5 5.5 Formula D 3.1 4.5 10 9.8 8.5 4.0 Formula E 2.6 4.58.5 8.2 8.0 5.0 Formula F 0.15 0.15 0.2 <0.1 <0.1 <0.1 Formula G 1.0 1.01.2 0.4 0.2 <0.1

As can be seen from these results, the formulas including compositionsof the present invention, i.e., Formulas A and B had much lower foamheights than Formulas C and D which included the non-peracid form of thesulfonated material, i.e., sulfonated oleic acid. The reduced foamheight of the compositions of the present invention is useful when usingthe compositions in applications where the production of foam isdetrimental to the application, for example, in a clean in placecleaning and/or sanitizing application.

Example 11 Laundry Sanitizing Compositions

A study was run to determine the ability of a composition of the presentinvention to sanitize laundry. A composition containing the sulfonatedperoleic acid product was tested against the commercially availablecleaning compositions Ozonit®, commercially available from Ecolab Inc.,and PAP-70®, available from Solvay. The compositions were tested againstStaphylococcus aureus ATCC 6538 and Pseudomonas aeruginosa ATCC 15442 at104° F. for 6 minutes. The test method was as follows. Fabric samplesthat had been rinsed with boiling water containing 300 grams sodiumcarbonate and 1.5 grams of a non-ionic wetting agent (e.g., TritonX-100), followed by a cold water rinse until all visible traces of thewetting agent were removed, were obtained. The fabric samples wereallowed to completely dry. The fabric samples were then autoclaved tosterilize them.

The test substances were then prepared, and the fabric samples wereinoculated with the test substances. The inoculated swatches were thendried. The samples were then secured in a laundrometer and agitated inwash water. The wash water was removed from the chamber of thelaundrometer, and the wash water and fabric samples are evaluated forthe reduction of the tested microorganism population.

The results are shown in the table below.

TABLE 19 Composition including Sulfonated Test/System Peroleic AcidProduct PAP-70 ® Ozonit ® Sanitizer Screen >3.82 >3.82 NA Disinfectant(Cloth 9 negative/9 total 9 negative/ 5 negative/ Carrier Screen) 9total 9 total

As can be seen from these results, both the composition of the presentinvention tested showed a greater than 3 log reduction in both the washwater and fabric carriers against P. aeruginosa and on the fabriccarriers against S. aureus.

The present invention also relates to novel compounds and the synthesisthereof Accordingly, the following examples are presented to illustratehow some of those compounds may be prepared.

Example 12 Stability Study

A study was performed to determine the stability of various sulfonatedperacids in aqueous solutions. The sulfonated peracids were comparedunder the same controlled conditions to determine how the structuraldifferences of the selected peracids impacted stability. The sulfonatedperacids studied included both mid-chain sulfonated and terminallysulfonated peracids.

Each peracid was tested at a concentration of 50 ppm under ambientconditions. Each individual solution was prepared from the correspondingperacid concentrate by adding it to a 0.05 M pH 5.0 citrate buffer, andadjusting the final solution pH to 5.0 with the addition of a smallamount of caustic. The terminally sulfonated peracids studied are shownin the table below.

Name Structure 2-Sulfoperoxyacetic acid (2-SPOAA)

5-sulfoperoxyheptanoic acid (5-SPOHA)

6-sulfoperoxyhexanoic acid (6-SPOHXA)

11-sulfoperoxyundecanoic acid (11- SPOUA)

The above terminally sulfonated peracids were compared to the mid-chainsulfonated peracid, persulfonated oleic acid product (PSOA), describedabove.

It should be noted however, that the precursor for the 11-SPOUA, viz.11-sulfoundecanoic acid, has limited solubility so less of the precursorwas used to make the sulfonated peracid studied. The same amount ofprecursor acid was used for making each of the other sulfonated peracidstested.

The peracid concentration over time was measured using a kineticiodometric titration method. The stability of each of the sulfonatedperacids is shown in FIG. 7. For comparison, 50 ppm peroxyacetic acid(POAA), at the same concentration and under the same conditions, wasalso included in the stability study. Based on the results seen in FIG.7, the half time of each individual peracid was estimated and theresults are summarized in the table below.

TABLE 20 Peracid 6- 11- POAA 2-SPOAA 5-SPOHA SPOHXA SPOUA PSOA t_(1/2)115 37 110 88 91 155 (hours)

As can be seen from the table above, 5-SPOHA, 6-SPOHXA, and 11-SPOUAhave similar stability profiles in aqueous solutions compared to that ofPOAA. The 2-SPOAA had a significantly shorter half life time.

Also as can be seen from these results, the stability of the mid-chainsulfonated PSOA was significantly better than that of POAA under thetested conditions. Without wishing to be bound by any particular theory,it is thought that the PSOA is the only peracid tested which hasdetergency, and which will form a micelle in an aqueous solution. Giventhat the sulfo group in the mid-chain sulfonated PSOA, is located nearthe center of the molecule, it is thought that the peroxycarboxylicportion is protected within a generally hydrophobic domain of vesiclesor related microstructures when PSOA is dissolved in water. This resultsin a substantially greater stability and longer half-life than theterminally sulfonated peracids.

Example 13 Bleaching Study

A study was performed to determine the bleaching properties of varioussulfonated percarboxylic acids in aqueous solutions. The sulfonatedperacids were compared to a surfactant/builder only control, as well asto peroxyacetic acid.

The following sulfonated peracids were tested: 2- Sulfoperoxyacetic acid(2-SPOAA); 5-sulfoperoxyheptanoic acid (5-SPOHA); 6-sulfoperoxyhexanoicacid (6-SPOHXA); 11-sulfoperoxyundecanoic acid (11-SPOUA); andsulfonated peroleic acid product (PSOA). The individual sulfonatedperacids were made, and allowed to incubate/equilibrate at 40° C. for 5to 7 days. After determining the peracid concentrations, the respectiveperacid solutions were normalized for potential available oxygen asdelivered by the peracids only. These solutions were tested for theirbleaching power at 100° F., pH 7 and in 5 grain hard water over a 20minute exposure. The table below shows the initial available oxygen fromeach peracid, as well as the percent of peracid titrated

TABLE 21 2- 5- 6- 11- Buffer Composition POAA* SPOAA SPOHA SPOHXA SPOUAPSOA Control Available Oxygen 32840 620 1300 1100 400 760 0 measured inperoxyacids' bleach concentrates formulae (ppm) Concentrate sample 0.1910.00 4.81 5.70 15.60 8.20 0 bleach solution Wt (g) Volume of buffer5.00** 5.00 5.00 5.00 5.00 5.00 5.00 concentrate used (8.5%/8.5%,NaHCO₃/ Na₂CO₃) (mL) Diluent (DI-H2O) mL 120 120 120 120 120 120 120Available Oxygen from 50 50 50 50 50 50 0 peroxyacids in bleachsolutions Total Bleach Use- 125 125 125 125 125 125 125 Solution Volume(mL) *POAA: Peroxyacetic acid **Required additional Acetic acid to reachpH target ~7.0

The sulfonated peracids were evaluated for their bleaching properties(also referred to herein as “soil removal” properties) by exposingsoiled swatches including: tea on 100% cotton; tea on a cotton-polyesterblend; and wine on 100% cotton. The soiled swatches were purchased fromTest Fabrics, Inc., West Pittston, Pa. The exposure of the swatches tothe various chemistries took place in a washing device known as aTerg-o-tometer (United States Testing Co., Hoboken, N.J.). The deviceprovides 6 stainless steel IL beakers immersed in a temperaturecontrolled water bath which was held at 100° F. for a 20 minutewash/bleach cycle. Each beaker includes an overhead agitator whichrotates 180 degrees before reversing at a frequency of 100 hz. Each testsolution contained sufficient bicarbonate-carbonate buffer to produce apH of approximately 7+/−0.5 units for the 20 minute wash cycle.

After completing the 20 minute wash cycle the fabric samples wereremoved and immediately rinsed with cold synthetic 5 grain water until 5cycles of fills and rinses were complete. The swatches were then laidflat and dried overnight on white polyester-cotton towels beforereflectance readings were taken using a spectrophotometer, e.g., HunterColorQuest XE (reflectance) Spectrophotometer.

To determine the percent (%) soil removal (SR), e.g., bleaching ability,the reflectance of the fabric sample was measured on aspectrophotometer. The “L value” is a direct reading supplied by thespectrophotometer. L generally is indicative of broad visible spectrumreflectance, where a value of 100% would be absolute white. The % soilremoval is calculated from the difference between the initial (beforewashing) lightness (L) value and the final L value (after washing):

SR=((L _(final) −L _(initial))/(96−L _(initial)))×100%

The results of the soil removal/bleaching test are shown in the tablebelow.

TABLE 22 POAA (Peroxyacetic 2- 5- 6- 11- Buffer Composition acid) SPOAASPOHA SPOHXA SPOUA PSOA Control SR (%) Tea on 100% 50 4 47 45 12 62 11cotton SR (%) Tea on cotton- 42 −2 46 45 10 65 4 poly blend SR (%) RedWine on 68 46 72 69 48 80 34 100% cotton

These results of the soil removal/bleaching test were also compared tothe POAA control. The results are shown in the table below.

TABLE 23 POAA Buffer (Peroxyacetic 2- 5- 6- 11- Control Compositionacid) SPOAA SPOHA SPOHXA SPOUA PSOA (BWC) SR (%) Tea on 0 −46 −3 −5 −3812 −39 100% cotton SR (%) Tea on 0 −44 3 2 −32 22 −39 cotton-poly blendSR (%) Red Wine 0 −22 4 1 −20 12 −34 on 100% cotton

FIG. 8 also graphically depicts these soil removal results relative tothe soil removal achieved with an equimolar amount of peroxyacetic acid.

As can be seen from these results, with respect to bleaching, only thePSOA, a mid-chain sulfonated peracid, produced a significant improvementover peroxyacetic acid. The other terminally sulfonated peracids testedresulted in only small improvements over peroxyacetic acid in somecases, and in most cases produced a negative effect relative toequimolar peroxyacetic acid.

Example 14 Coupling Ability Study

A study was performed to determine the coupling/hydrotropic propertiesof various sulfonated peracids in aqueous solutions. The ability of theselected peracids to couple octanoic acid was measured.

The following sulfonated peracids were tested: 2- Sulfoperoxyacetic acid(2-SPOAA); 5-sulfoperoxyheptanoic acid (5-SPOHA); 6-sulfoperoxyhexanoicacid (6-SPOHXA); 11-sulfoperoxyundecanoic acid (11-SPOUA); andsulfonated peroleic acid product (PSOA). Twenty grams (20 g) of eachperacid solution was diluted into a beaker containing hydrogen peroxide.Each peracid dissolved completely, except for 11-SPOUA which dissolvedonly partially. To each of these solutions, 0.4 grams of 1-octanoic acidwas added. The octanoic acid initially floated to the tops of thesolutions. The solutions were then stirred for 5-10 minutes withmagnetic stir bars at 1,000 rpm. The solutions were then centrifuged for20 minutes at 3,000-5,000 rpm. The lower phase of each solution was thencollected. The lower phases were further clarified by filtration through0.45 micron syringe filters. All of the filtrates appeared clear andhomogenous. The filtered solutions were analyzed by liquidchromatography for 1-octaonic acid. The results are shown in the tablebelow.

TABLE 23 Solution 1-Octanoic acid (ppm) 2-SPOAA 160 5-SPOHA 230 6-SPOHXA240 11-SPOUA 890 PSOA 13,200

As can be seen from these results, the mid-chain sulfonated peracid,PSOA, showed a far greater coupling ability for coupling octanoic acidcompared to the other terminally sulfonated peracids tested. Themid-chain sulfonated PSOA had approximately a 1300% greater ability tocouple octanoic acid compared to the next closest sulfonated peracid,11-SPOUA.

Example 15 Contact Angle Study

A study was performed to measure the wetting properties of varioussulfonated peracids in aqueous solutions, by measuring the contact angleof the individual solution on different surfaces.

The following sulfonated peracids were tested: 2- Sulfoperoxyacetic acid(2-SPOAA); 5-sulfoperoxyheptanoic acid (5-SPOHA); 6-sulfoperoxyhexanoicacid (6-SPOHXA); 11-sulfoperoxyundecanoic acid (11-SPOUA); andsulfonated peroleic acid product (PSOA).

A FTA32 Contact Angle Goniometer with image processing by FTA 32software was used to measure the contact angle. The contact angle wasmeasured on both stainless steel, and polypropylene surfaces. Theperacid concentrates shown in the table below were diluted 250 timeswith DI water. However, the 11-SPOUA was diluted 85 times with DI water,given the lower levels of peracid precursor in the formula.

TABLE 24 2- 5- 6- 11- Composition SPOAA SPOHA SPOHXA SPOUA PSOA ControlPeracid 0.38% 1.02% 0.97% 0.41% 1.27% na Titrated

The table below shows the contact angle observed for the tested peracidson both stainless steel and polypropylene surfaces. The results shownare the average of at least three contact angle measurements.

TABLE 25 Contact Angle (degree) Solution Stainless Steel Polypropylene2-SPOAA 77 75 5-SPOHA 68 75 6-SPOHXA 77 84 11-SPOUA 72 77 PSOA 52 56Control 81 79

As can be seen from these results, only the mid-chain sulfonated PSOAhad a significantly lower contact angle on both surfaces tested,compared to the control. The PSOA had about a 36% lower contact anglethan the control on the stainless steel surface, and about a 29% lowercontact angle than the control on the polypropylene surface. Withoutwishing to be bound by any particular theory, it is thought that a lowercontact angle indicates a greater wetting ability, resulting in greaterdetergency.

Example 16 Antimicrobial Study

A study was performed to determine the antimicrobial efficacy of varioussulfonated peracids. Use solutions containing 100 ppm of the followingpersulfonated acids were tested: 2-sulfoperoxyacetic acid (2-SPOAA);5-sulfoperoxyheptanoic acid (5-SPOHA); 6-sulfoperoxyhexanoic acid(6-SPOHXA); 11-sulfoperoxyundecanoic acid (11-SPOUA); and sulfonatedperoleic acid product (PSOA).

The use solutions were tested against Staphylococcus aureus ATCC 6538and Escherichia coli ATCC 11229. The following test procedure was used.First, 99 ml of the persulfonated acid to be tested was dispensed into a250 ml flask. The liquid was allowed to equilibrate to 25±1° C. Theliquid was then swirled in the flask and 1 ml of a 10¹⁰ CFU/ml of thetest bacteria was added to the beaker. After the desired exposure time,1 mL of the combined peracid/bacteria solution was removed from theflask. The removed solution was then placed in 9 mls of an appropriateneutralizer. The desired dilution was then plated and allowed toincubate at 35° C. for 48 hours. The plates are then read to determinethe reduction in microbial count. For this experiment, samples weretested over 90 seconds total exposure time, at 10 second intervals.

The results are shown in FIGS. 9 and 10. These figures show the ratiobetween the survivors (N) and the initial inoculum numbers (N0) at agive time point. For example, if the ratio of survivors (N) to theinitial inoculum numbers (N0) is 1.0, no antimicrobial activity isachieved. As the rate approaches zero, complete kill is achieved. FIG. 9graphically depicts the efficacy of the tested persulfonated acidsagainst Staphylococcus aureus at ambient temperature. As can be seenfrom this Figure, the mid-chain sulfonated PSOA had a significantlyhigher reduction in the population of S. aureus than the otherterminally sulfonated peracids tested, both initially (at 10 seconds),and over the course of the time tested.

FIG. 10 graphically depicts the efficacy of the tested persulfonatedacids against Escherichia coli at ambient temperature. As can be seenfrom this Figure, the mid-chain sulfonated PSOA had a significantlyhigher reduction in the population of E. coli at 90 seconds, compared tothe short chain, terminally sulfonated peracids tested. Thus, overall,it was observed that mid-chain sulfonated peracids are more effective atreducing populations of S. aureus, and E. coli.

Synthesis of Selected Compounds of the Invention

Preparation of the Sulfonated Peroleic Acid Product.

417.8 g of OA5-R (Intertrade Organic's, 40% active Sulfonated Oleicacid) was added to a 2-L beaker immersed in a large ice-bath, to whichwas subsequently added, 66.4 g of Dequest 2010 (60% activeHydroxyethylenediphosphonic acid, Monsanto) and 535 g of Hydrogenperoxide (46% active, Solvay-Interox). The beaker was fitted with amagnetic stir bar and the solution was stirred aggressively while adding940 g of sulfuric acid (96% active, Mallinkrodt). The rate of thesulfuric acid addition was controlled to produce a 120° F. exotherm inthe reaction solution, and while this was occasionally exceeded byseveral degrees F., it wasn't allowed to exceed 125° F. Several minutesafter completing the sulfuric acid addition, the ice bath was removedand the heterogenous solution was stirred for 72 hours allowing thetemperature to equilibrate to ambient (70° F.) conditions.

Several hours after discontinuing the stirring, the two phase reactionsolution was added to a separatory funnel and the upper and lower phasewere separated. 239.4 g of upper phase were collected and the upperphase was further purified by centrifugation at 3000 rpm for 10 minutes.The final upper phase yield was 206 g and titrated as 60% Peroxyacidbased upon an assumed molecular weight of 412 (theoretical yield 178 g).In addition the upper phase contained 1.8% Hydrogen peroxide. Acentrifuged lower phase sample titrated as 14% Peroxyacid (MW 412) and8.8% hydrogen peroxide.

Synthesis of 11-Sulfoundecanoic Acid and 10,11-Disulfoundecanoic Acid

11-Sulfoundecanoic acid: Deionized water (150 ml), isopropyl alcohol(200ml) and 11-undecylenic acid (28.56 g, 0.155 mol) were placed in a 1.0liter flask equipped with stirrer, additional funnel, reflux condenser,thermometer and a gas inlet tube. To the additional funnel was added apremix which contained 15.2 g (0.08 mol) of sodium metabisulfite and1.28 g of NaOH in 55 g of water. The whole device was purged withnitrogen gently. After heating to reflux (82° C.), a small portion oft-butl perbenzoate (out of total amount of 0.5 g, 2.5 mmol) was added tothe flask. Then the sodium metabisulfite/NaOH premix was addedcontinuously over a five hour period to the reaction solution through anaddition funnel. The remaining t-butl perbenzoate was also added insmall portions during this time.

The solvent was then removed under reduced pressure using a rotavapour,and the residue washed with acetone, and dried, yielding 31.0 g of whitesolid. NMR analysis of the solid indicated no presence of the residualraw materials. The white solid obtained was dissolved in hot water (100ml, 75° C.), and neutralized to pH 5.5 with NaOH. Then 2.0 g of 50% H₂O₂was added to the solution. The solution was then allowed to cool down toroom temperature, and the solid precipitated was filtered, washed withcold water, and dried, affording 21.0 g of white solid, characterized aspure 11-sulfoundecanoic acid. ¹³C NMR (D₂O): 180, 51, 34, 28-29(multiple), 27.5, 24.5, 24 ppm. MS (ESI): 265.1 (M⁺−H).

10,11-Disulfoundecanoic acid: this compound was obtained as a byproductfrom the 11-Sulfoundecanoic acid reaction as described above. Thefiltrate, after collecting 11-sulfoundecanoic acid through filtration,was concentrated to ˜50 ml when precipitate start to form. The mixturewas cooled down in the refrigerator, and the additional solid formed wasfiltered, washed with a small amount of ice water, and dried, yielding5.0 g of white solid. ¹³C NMR (D₂O): 184, 57, 51.5, 37.5, 28-29(multiple), 27.5, 26, 24 ppm. MS (ESI): 345.0.

Synthesis of 11-Sulfoundecaneperoxoic acid (Compound D) and10,11-Disulfoundecaneperoxoic Acid (Compound E)

11- Sulfoperoxyundecanoic Acid:

1.3 g of 11-sulfoundecanoic acid was dissolved in 2.5 g of 98% sulfuricacid. To this solution (the temperature of the solution did not exceed60° C.) 1.5 g of 50% H₂O₂ was added, and the resulting mixture wasstirred at room temperature for 1.5 hr. At this point, a white solidprecipitated from the solution. The mixture was reheated to 50° C. witha water bath until the solution was clear. The solution was then stirredat room temperature for 0.5 hr, and cooled down in the freezer. Then 20ml of ice water was added to the mixture, and the solid filtered, washedwith ice water, and dried under vacuum, yielding 0.6 g of a white solid.¹³C NMR (D₂O): 176, 51.5, 30.5, 27.5-29 (multiple), 24.5, 24 ppm. MS(ESI): 281.5 (M⁻−H). Available oxygen (iodometric): 5.41% (theoretical:5.64%).

10,11- Disulfoundecaneperoxoic Acid (Compound E)

To 1.5 g of 10,11-disulfoundecanoic acid was added 2.5 g of 96% H₂SO₄,and the mixture was stirred at room temperature. Then 1.0 g of 50% H₂O₂was added slowly (the temperature not exceeding 60° C.) to the mixture,and after addition, the mixture was heated to 50° C. with water bath,and the solution stirred for 2.0 hrs. The solution was then cooled downin the freezer, and 20 ml of ice water was added with stirring. Thesolid precipitated was filtered, washed with ice water, and dried undervacuum, affording 1.0 g of white solid. ¹³C NMR (D₂O): 175.5, 57, 30.5,27.5-29 (multiple), 24.5, 24 ppm. Available oxygen (iodometric): 4.10%(theoretical: 4.41%).

Synthesis of 9/10-Sulfostearic Acid (Sulfonated Stearic Acid)

Deionized water (150 ml), isopropyl alcohol (200 ml) and oleic acid(43.78 g, 0.155 mol) were placed in a 1.0 liter flask equipped withstirrer, additional funnel, reflux condenser, thermometer and a gasinlet tube. To the additional funnel was added a premix which contained15.2 g (0.08 mol) of sodium metabisulfite (Na₂S₂O₅) and 1.28 g of NaOHin 55 g of water. The whole device was bubbled gently with nitrogen.After heating to reflux (82° C.), a small portion of t-butl perbenzoate(out of total amount of 0.5 g, 2.5 mmol) was added to the flask. Thenthe Na₂S₂O₅/NaOH premix was added through the addition funnelcontinuously over the course of five hours. The remaining t-butlperbenzoate was also added in portions during this time.

The solvent was then removed under reduced pressure using rotavapour. Tothe residue was added 100 ml of DI water, the pH of the solution wasadjusted to 2.5 with H₂SO₄. The resulting mixture/solution wastransferred to a separation funnel, and the top oily layer (non reactedoleic acid) was removed. The aqueous layer was extracted with petroleumether (2×50 ml), and after removal of the water, afforded 12.5 g ofwhite waxy solid. ¹³C NMR (D₂O): 179, 60, 34.5, 32, 28.5-30 (multiple),24.5, 22.5, 14 ppm. MS (ESI): 363.4 (M⁺−H).

Preparation of 9/10-Sulfoperoxystearic Acid (in Formulation)

To a 2.0 g mixture of 9 or 10-Sulfostearic acid was added 2.0 g of 50%H₂O₂. The mixture was stirred at room temperature until all the solidwas dissolved. Then, 2.0 g of 75% H₃PO₄ was added, and the resultingsolution was stirred at room temperature overnight. No attempt was madeto isolate the pure 9 or 10-sulfoperoxystearic acid from solution. ¹³CNMR (D₂O) of the solution showed a peracid peak (COOOH) at 174 ppm andthe parent the carboxylic acid peak at 178 ppm. The iodometric titration(QATM-202) indicated 18.96% of sulfoperoxystearic acid.

1. A compound according to Formula I:

wherein: R₁ is a substituted or unsubstituted C_(m) alkyl group; R₂ is asubstituted or unsubstituted C_(n) alkyl group; X is hydrogen, acationic group, or an ester forming moiety; n is 1 to 10; m is 1 to 10;and m+n is less than or equal to 18, or salts or esters thereof.
 2. Thecompound of claim 1, wherein R₁ is an unsubstituted C₉ alkyl group. 3.The compound of claim 1, wherein R₁ is a substituted C₉ alkyl group. 4.The compound of claim 1, wherein R₁ is a substituted C₁₀ alkyl group. 5.The compound of claim 3, wherein the substituted C₉ alkyl group issubstituted with one or more hydroxyl groups.
 6. The compound of claim4, wherein at least two of the carbons on the carbon backbone of thealkyl group form a heterocylic group.
 7. The compound of claim 1,wherein R₁ is a C₈-C₉ alkyl, and R₂ is a C₇-C₈ alkyl.
 8. The compound ofclaim 1, wherein said compound is selected from the group consisting of:

salts, esters, and mixtures thereof.
 9. A composition comprising acompound according to Formula I:

wherein: R₁ is a substituted or unsubstituted C_(m) alkyl group; R₂ is asubstituted or unsubstituted C_(n) alkyl group; X is hydrogen, acationic group, or an ester forming moiety; n is 1 to 10; m is 1 to 10;and m+n is less than or equal to 18, or salts, esters, or mixturesthereof.
 10. The composition of claim 9, wherein said compound isselected from the group consisting of:

salts, esters, and mixtures and derivatives thereof.
 11. The compositionof claim 9, wherein the composition includes at least one of10-hydroxy-9-sulfootacdecaneperoxoic acid,10,11-dihydroxy-9-sulfooctadecaneperoxoic acid,9-hydroxy-10-sulfooctadecaneperoxoic acid, and10-sulfo-8,9-dihydroxyoctadecaneperoxoic acid.
 12. The composition ofclaim 9, wherein the pH of the composition is less than about
 9. 13. Thecompositions of claim 9, wherein the compound is present at about 10 ppmto about 100 wt %.
 14. The composition of claim 9, wherein the compoundis present at about 0.1 wt % to about 10 wt %.
 15. The composition ofclaim 9, wherein the compound is present at about 1 wt % to about 5 wt%.
 16. The composition of claim 9, wherein the compound is present at aneffective antimicrobial amount.
 17. The composition of claim 16, whereinthe compound is present at about 10 ppm to about 100 ppm.
 18. Thecomposition of claim 9, wherein the compound is present in an amounteffective for killing one or more of a food-borne pathogenic or spoilagebacteria associated with a food product.
 19. The composition of claim18, wherein the food product is selected from the group consisting ofmeat, meat products, seafood, poultry, poultry products, produce, eggs,living eggs, egg products, ready to eat food, wheat, seeds, roots,tubers, leafs, stems, corns, flowers, sprouts, seasonings, andcombinations thereof.
 20. The composition of claim 18, wherein thebacteria is selected from the group consisting of Salmonellatyphimurium, Salmonella javiana, Campylocater jejuin, Listeriamonocytogenes, Escheriachia coli 0157:H7, yeast, mold, and mixturesthereof.
 21. The composition of claim 9, wherein the compound is presentin an amount effective for reducing a population of a microorganismselected from the group consisting of spores, bacteria, mold, yeast,viruses and mixtures thereof.
 22. The composition of claim 21, whereinthe microorganism is selected from the group consisting ofStaphylococcus aureus, Pseudomonas aeruginosa, methicillin-resistantStaphylococcus aureus and mixtures thereof.
 23. The composition of claim21, wherein the microorganism is selected from the group consisting ofBacillus subtilis, Bacillus cereus, Clostridium sporogenes, Clostridiumbotulinum, Clostridium difficile, Clostridium sporogenes and mixturesthereof.
 24. The composition of claim 21, wherein the microorganism isselected from the group consisting of poliovirus, mycobacteriumtuberculosis and mixtures thereof.
 25. The composition of claim 9,wherein the composition further comprises an oxidizing agent.
 26. Thecomposition of claim 25, wherein the oxidizing agent comprises hydrogenperoxide.
 27. The composition of claim 25, wherein the compositionfurther comprises at least one C₁ to C₂₂ peroxycarboxylic acid.
 28. Thecomposition of claim 27, wherein the peroxycarboxylic acid comprises atleast one C5 to C11 peroxycarboxylic acid.
 29. The composition of claim28, wherein the peroxycarboxylic acid comprises peroxyoctanoic acid. 30.The composition of claim 29, wherein the peroxyoctanoic acid is presentat about 0.1 wt % to about 10 wt %.
 31. The composition of claim 27,wherein the peroxycarboxylic acid comprises peroxyacetic acid.
 32. Thecomposition of claim 31, wherein the peroxyacetic acid is present atabout 1 wt % to about 10 wt %.
 33. The composition of claim 27, whereinthe composition further comprises at least one carboxylic acid.
 34. Thecomposition of claim 33, wherein carboxylic acid is at least one C5 toC11 carboxylic acid.
 35. The composition of claim 27, wherein thecomposition comprises at least one C1 to C4 peroxycarboxylic acid and atleast one C5 to C11 carboxylic acid.
 36. A method for sanitizing anarticle comprising contacting the article with the composition accordingto claim
 9. 37. The method of claim 36, wherein the article is selectedfrom the group consisting of medical or surgical devices, textiles,architectural surfaces, hard surface packaging, dishware andcombinations thereof.
 38. A method for removing soil from an articlecomprising contacting the surface with the composition according toclaim
 9. 39. The method of claim 38, wherein the article comprisesdishware.
 40. The method of claim 38, wherein the article compriseslaundry.
 41. The method of claim 40, wherein the step of contactingcomprises contacting the laundry with the composition at a temperatureof between about 4° C. to about 80° C.
 42. A method for reducing apopulation of a microorganism on a surface comprising contacting thesurface with the composition according to claim
 11. 43. The method ofclaim 42, wherein the microorganism is selected from the groupconsisting of spores, bacteria, mold, yeast, viruses and mixturesthereof.
 44. The method of claim 42, wherein the microorganism isselected from the group consisting of Staphylococcus aureus, Pseudomonasaeruginosa, methicillin-resistant Staphylococcus aureus and mixturesthereof.
 45. The method of claim 42, wherein the composition is presentin an amount effective to produce a 5 log reduction in the microorganismpopulation in about 5 minutes at about 40° C.
 46. The method of claim42, wherein the composition is present at at least about 10 ppm.
 47. Themethod of claim 42, wherein the composition is present at between about10 ppm and about 2000 ppm.
 48. The method of claim 42, wherein themicroorganism is selected from the group consisting of Bacillussubtilis, Bacillus cereus, Clostridium sporogenes, Clostridiumbotulinum, Clostridium difficile, Clostridium sporogenes and mixturesthereof.
 49. The method of claim 42, wherein the microorganism isselected from the group consisting of poliovirus, mycobacteriumtuberculosis and mixtures thereof.
 50. The method of claim 45, whereinthe bacteria is selected from the group consisting of Salmonellatyphimurium, Salmonella javiana, Campylocater jejuin, Listeriamonocytogenes, Escheriachia coli 0157:H7, yeast, mold, and mixturesthereof.
 51. A method for bleaching an article comprising contacting thearticle with a composition comprising a compound of claim
 1. 52. Themethod of claim 51, wherein the article is a hard surface.
 53. Themethod of claim 51, wherein the article is a textile.
 54. An aqueous,antimicrobial bleaching composition comprising: a) a compound accordingto Formula I:

wherein: R₁ is a substituted or unsubstituted C_(m) alkyl group; R₂ is asubstituted or unsubstituted C_(n) alkyl group; X is hydrogen, acationic group, or an ester forming moiety; n is 1 to 10; m is 1 to 10;and m+n is less than or equal to 18, or salts or esters thereof, (b) aC₁ to C₄ carboxylic acid; (c) a C₅ to C₁₁ carboxylic acid; and (d) anoxidizing agent wherein the pH of the composition is about 7 to about14.
 55. The composition of claim 54, wherein the C₁ to C₄ carboxylicacid is acetic acid.
 56. The composition of claim 54, wherein the C₅ toC₁₁ carboxylic acid is octanoic acid.
 57. The composition of claim 54,wherein the compound of Formula I is selected from the group consistingof:

and mixtures and derivatives thereof.
 58. The composition of claim 54,wherein the compound of Formula I includes at least one of includes atleast one of 10-hydroxy-9-sulfootacdecaneperoxoic acid,10,11-dihydroxy-9-sulfooctadecaneperoxoic acid,9-hydroxy-10-sulfooctadecaneperoxoic acid, and10-sulfo-8,9-dihydroxyoctadecaneperoxoic acid.
 59. The composition ofclaim 54, wherein the composition is stable at 122° F. for at leastabout 4 weeks.
 60. The composition of claim 54, wherein the oxidizingagent comprises hydrogen peroxide.
 61. The composition of claim 54,further comprising a stabilizing agent.
 62. The composition of claim 61,wherein the stabilizing agent is selected from the group consisting oforganic amino polyphosphonic acid complexing agents, organic hydroxylpolyphosphonic acid complexing agents, and mixtures thereof.
 63. Thecomposition of claim 61, wherein the stabilizing agent is selected fromthe group consisting of carboxylic acids, hydroxycarboxylic acids,aminocarboxylic acids, heterocyclic carboxylic acids and mixturesthereof.
 64. The composition of claim 54, wherein the composition issubstantially phosphorous free.
 65. The composition of claim 54, whereinthe composition comprises: (a) about 1 wt % to about 5 wt % of acompound according to Formula I; (b) about 1 wt % to about 10 wt % ofthe C₁ to C₄ carboxylic acid; (c) about 1 wt % to about 10 wt % of theC₅ to C₁₁ carboxylic acid; and (d) about 10 wt % to about 30 wt % of theoxidizing agent.
 66. A method for treating laundry, the methodcomprising: (a) applying the composition according to claim 54 to thelaundry; (b) draining the composition from the laundry.
 67. The methodof claim 66, wherein the laundry is treated at about 100° F.
 68. Themethod of claim 66, wherein the treatment is selected from the groupconsisting of sanitizing the laundry, disinfecting the laundry, andcombinations thereof.
 69. The method of claim 66, wherein the treatmentcomprises bleaching the laundry.
 70. A method for reducing a populationof organisms on a surface comprising contacting the surface with thecomposition of claim
 54. 71. The method of claim 70, wherein theorganism is selected from the group consisting of spores, bacteria,mold, yeast, viruses, and combinations thereof.
 72. An aqueous sanitizercomprising: (a) a compound according to Formula I

wherein: R₁ a substituted or unsubstituted C_(m) alkyl group; R₂ is asubstituted or unsubstituted C_(n) alkyl group; X is hydrogen, acationic group, or an ester forming moiety; n is 1 to 10; m is 1 to 10;and m+n is less than or equal to 18, or salts or esters thereof; and (b)an acidulant; and (c) an oxidizing agent.
 73. The composition of claim72, wherein the compound is selected from the group consisting of:

and salts, esters, and mixtures thereof.
 74. The composition of claim72, wherein the oxidizing agent comprises hydrogen peroxide.
 75. Thecomposition of claim 72, wherein the acidulant is selected from thegroup consisting of sulfuric acid, sodium bisulfate, nitric acid,hydrochloric acid and combinations thereof.
 76. The composition of claim72, wherein the acidulant is selected from the group consisting ofmethane sulfonic acid, ethane sulfonic acid, propane sulfonic acid,butane sulfonic acid, xylene sulfonic acid, benzene sulfonic acid,formic acid, acetic acid, halocarboxylic acids, picolinic acid,dipicolinic acid, and mixtures thereof.
 77. The composition of claim 72,further comprising a stabilizing agent.
 78. The composition of claim 77,wherein the stabilizing agent is selected from the group consisting oforganic amino polyphosphonic acid complexing agents, organic hydroxylpolyphosphonic acid complexing agents, and mixtures thereof.
 79. Thecomposition of claim 77, wherein the stabilizing agent is selected fromthe group consisting of carboxylic acids, hydroxycarboxylic acids,aminocarboxylic acids, heterocyclic carboxylic acids and mixturesthereof.
 80. The composition of claim 72, wherein the composition issubstantially phosphorous free.
 81. The composition of claim 72, furthercomprising a surfactant.
 82. The composition of claim 81, wherein thesurfactant is selected from the group consisting of alkyl sulfonates,aromatic sulfonates, and mixtures thereof.
 83. A method for sanitizing asurface using a clean in place process comprising contacting the surfacewith the composition of claim
 72. 84. A method of manufacturing acompound of claim 1, said method comprising: (a) contacting a non-alphasulfonated carboxylic acid with an oxidizing agent under acidic pHconditions to produce a sulfoperoxycarboxylic acid.
 85. A use solutioncomprising a compound according to Formula I

wherein: R₁ is a substituted or unsubstituted C_(m) alkyl group; R₂ is asubstituted or unsubstituted C_(n) alkyl group; X is hydrogen, acationic group, or an ester forming moiety; n is 1 to 10; m is 1 to 10;and m+n is less than or equal to 18, or salts or esters thereof; whereinthe use solution is stable at room temperature for about 14 days at a pHof about 6.5